1(3H)-Isobenzofuranone,3-methyl-(9CI) synthesis
- Product Name:1(3H)-Isobenzofuranone,3-methyl-(9CI)
- CAS Number:3453-64-3
- Molecular formula:C9H8O2
- Molecular Weight:148.16
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Yield: 94%
Reaction Conditions:
with dirhodium tetraacetate;1,3-bis-(diphenylphosphino)propane;scandium tris(trifluoromethanesulfonate) in 1,4-dioxane;water at 100; for 16 h;
Steps:
2.3 A typical procedure of ketone hydroacylation catalyzed by Rh(II) catalyst (Table. 2, entry 1)
General procedure: 2-Benzoylbenzaldehyde 1a (84.1 mg, 0.4 mmol) was dissolved in dioxane (0.5 mL) and an aqueous solution of Sc(OTf)3 (4.0 μmol, 0.1 mL of 19.7 mg/mL solution of water) was added. To this mixture, Rh(II)-dppp stock solution (shown in 2.1, 0.6 mL) was added and the mixture was stirred at 100 °C under air for 16 h. After the mixture was diluted with EtOAc, the organic phase was washed with water, dried over Na2SO4, and filtered. The solvent was removed in vacuo and the conversion of 1a and the yield of 2a was determined by 1H NMR analysis with reference to an internal standard (1,1,2,2-tetrachloroethane). The crude product was purified by column chromatography packed with silica gel and small amount of amino silica gel (hexane/acetone = 10:1 to3:1) to afford the pure product 2a (76.7 mg, 92% yield).
References:
Yasukawa, Tomohiro;Kobayashi, Shu [Chemistry Letters,2017,vol. 46,# 1,p. 98 - 100] Location in patent:supporting information
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