5-Methoxyfuran-2(5H)-one → 6,6-dimethyl-4(RS)-methoxy-3-oxabicyclo (3,1,0) hexan-2-one

HRID 2292273Notes

Reaction equation

HRID 2292273 reaction equation
[CH3:1][O:2][CH:3]1[O:7][C:6](=[O:8])[CH:5]=[CH:4]1.[C:9]1(S(C2C=CC=CC=2)=C(C)C)[CH:14]=CC=C[CH:10]=1>CO>[CH3:10][C:9]1([CH3:14])[CH:5]2[CH:4]1[CH:3]([O:2][CH3:1])[O:7][C:6]2=[O:8]

Participants

4

Reactant 2

HCID 1120425-Methoxyfuran-2(5H)-oneHCID 11138905Diphenyl isopropylidene sulfurane

Product 1

HCID 129227176,6-dimethyl-4(RS)-methoxy-3-oxabicyclo (3,1,0) hexan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a preferred embodiment of the invention, the alcohol ZOH is methanol and the 5(RS)-methoxy-2,5-dihydrofuran-2-one is reacted with diphenyl isopropylidene sulfurane to obtain (1RS, 5SR) 6,6-dimethyl-4(RS)-methoxy-3-oxabicyclo (3,1,0) hexan-2-one which is then subjected to acid hydrolysis to obtain (1RS, 5SR) 6,6-dimethyl-4(RS)-hydroxy-3-oxabicyclo (3,1,0) hexan-2-one.

Sources & evidence

ORD record
ord-d5853e3dd0a44beabb6bdd6ee24c84a4
Source dataset
uspto-grants-1989_01
Patent number
US04801723

Reaction notes

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