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| | (TERT-BUTYLDIMETHYLSILYLOXY)ACETALDEHYDE Basic information |
| | (TERT-BUTYLDIMETHYLSILYLOXY)ACETALDEHYDE Chemical Properties |
| Melting point | 165-167 ºC | | Boiling point | 165-167 °C(lit.) | | density | 0.915 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.432(lit.) | | Fp | 140 °F | | storage temp. | 2-8°C | | form | Powder | | color | White to light beige to grey | | Specific Gravity | 0.915 | | Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents | | InChI | InChI=1S/C8H18O2Si/c1-8(2,3)11(4,5)10-7-6-9/h6H,7H2,1-5H3 | | InChIKey | MEBFFOKESLAUSJ-UHFFFAOYSA-N | | SMILES | C(=O)CO[Si](C(C)(C)C)(C)C |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | RIDADR | UN 1989 3/PG 3 | | WGK Germany | 3 | | TSCA | No | | HazardClass | 3 | | HS Code | 29319090 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Eye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2
STOT SE 3 |
| | (TERT-BUTYLDIMETHYLSILYLOXY)ACETALDEHYDE Usage And Synthesis |
| Chemical Properties | Clear colorless to straw colored liquid | | Uses | Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (–)-dactylodide. | | Synthesis | Oxalyl chloride (13.7 mL, 162.2 mmol) was dissolved in anhydrous dichloromethane (400 mL) under nitrogen protection and cooled to -78°C. Dimethyl sulfoxide (25.1 mL, 353.9 mmol) was added slowly and stirred for 30 minutes. Subsequently, a solution of 2-((tert-butyldimethylsilyl)oxy)ethanol (26.0 g, 147.5 mmol) in anhydrous dichloromethane (100 mL) was added dropwise. After maintaining -78 °C and continuing to stir for 30 min, triethylamine (102.74 mL, 737.0 mmol) was added slowly and dropwise. The reaction mixture was stirred at -78 °C for another 30 min, then gradually warmed up to room temperature and continued stirring for 1 h. The reaction mixture was then stirred at -78 °C for 1 h. The reaction mixture was then gradually warmed up to room temperature. The pH of the reaction mixture was adjusted to 4 with aqueous 2N hydrochloric acid and then extracted with dichloromethane (3 x 400 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-((tert-butyldimethylsilyl)oxy)acetaldehyde (34.0 g, 100%) as a colorless oil. The product can be used directly in the subsequent reaction without further purification. | | References | [1] Organic Letters, 2016, vol. 18, # 18, p. 4534 - 4537
[2] Patent: WO2017/24018, 2017, A1. Location in patent: Paragraph 00132
[3] Patent: US2016/122345, 2016, A1. Location in patent: Paragraph 0115; 0118
[4] Patent: US9481674, 2016, B1. Location in patent: Page/Page column 47; 48
[5] Patent: WO2017/87608, 2017, A1. Location in patent: Paragraph 00125; 00128 |
| | (TERT-BUTYLDIMETHYLSILYLOXY)ACETALDEHYDE Preparation Products And Raw materials |
| Raw materials | 4,9-Dioxa-3,10-disiladodec-6-ene, 2,2,3,3,10,10,11,11-octamethyl-, (6Z)--->(TERT.-BUTYLDIMETHYLSILYLOXY)ETHANOL-->4,9-Dioxa-3,10-disiladodec-6-ene, 2,2,3,3,10,10,11,11-octamethyl--->Triethylamine-->Dimethyl sulfoxide-->Dichloromethane-->Oxalyl chloride | | Preparation Products | (S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide-->(E)-4-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-2-butenoic Acid Ethyl Ester |
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