ChemicalBook CAS DataBase List 3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-1-PROPANAL

3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-1-PROPANAL synthesis

11synthesis methods

Product Name:3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-1-PROPANAL
CAS Number:89922-82-7
Molecular formula:C9H20O2Si
Molecular Weight:188.34

3-(tert-Butyldimethylsilyloxy)propanol (1.90 g, 10 mmol) was dissolved in dichloromethane (20 mL), and Dess-Martin reagent (6.36 g, 15 mmol) was added under ice bath. After stirring at room temperature for 4 hours, saturated aqueous sodium bicarbonate solution was added to quench, and the mixture was diluted with dichloromethane (100 mL). The mixture was washed twice with saturated aqueous sodium bicarbonate solution and once with brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The mixture was purified by silica gel column chromatography to obtain 1.55 g of 3-[(tert-Butyldimethylsilyl)oxy]-1-propanal with a yield of 82%.

3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-1-PROPANAL synthesis route

114615-82-6
223 suppliers
$8.00/100mg

73842-99-6 Synthesis

73842-99-6
127 suppliers
$6.00/1g

3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-1-PROPANAL

89922-82-7
96 suppliers
$13.00/100mg

Yield:89922-82-7 66%

Reaction Conditions:

with 4-methylmorpholine N-oxide;silica gel in dichloromethane;acetonitrile

Steps:

1.1 Step 1
Step 1 Tetrapropylammonium perruthenate (0.18 g, 5.3 mmol) was added to a mixture of methylene chloride (20 mL) and acetonitrile (2 mL) containing 3-(tert-butyldimethylsilyloxy)-propanol (2 g, 0.01 mmol), N-methylmorpholine N-oxide (1.76 g) and 4 Å molecular sieves. The reaction mixture was stirred at RT overnight and then filtered through a pad of silica gel. The filtrate was concentrated under vacuo to afford 3-(tert-butyldimethylsilyloxy)-propionaldehyde (1.3 g, 66%).

References:

Syntex (U.S.A.) LLC US2003/176484, 2003, A1

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73842-99-6 Synthesis

73842-99-6
127 suppliers
$6.00/1g

89922-82-7
96 suppliers
$13.00/100mg

References