6,6-Dimethyl-3-oxabicyclo[3.1.0]hexan-2-one → (1r,5s)-6,6-Dimethyl-3-oxabicyclo[3.1.0]hexan-2-one

HRID 2078490Notes

Reaction equation

HRID 2078490 reaction equation
[CH3:1][C:2]1([CH3:9])[CH:7]2[CH:3]1[CH2:4][O:5][C:6]2=[O:8].OC[C@H]1[C@H](C(O)=O)C1(C)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[C@H:7]2[C@@H:3]1[CH2:4][O:5][C:6]2=[O:8]

Participants

4

Reactant 2

HCID 118153586,6-Dimethyl-3-oxabicyclo[3.1.0]hexan-2-oneHCID 67120920(1S,3S)-3-(Hydroxymethyl)-2,2-dimethylcyclopropane-1-carboxylic acid

Product 1

HCID 11094620(1r,5s)-6,6-Dimethyl-3-oxabicyclo[3.1.0]hexan-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.46 g of a solution containing 1.20 g of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one (9.49 mmol, yield based on ethyl cis-3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate: 99.4%, (1R, 5S)-body had an optical purity of 92.8% ee) was obtained in the same manner as in Example 7 excepting that pH was 1 in extracting 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one with toluene in Example 2. In this toluene solution, 0.062 g (0.43 mmol) of trans-3-hydroxymethyl-2,2-dimethylcyclopropanecarboxylic acid was present.

Workup

  1. customyield
  2. customwas obtained in the same manner as in Example 7 excepting that pH was 1
  3. extractionin extracting 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one with toluene in Example 2

Sources & evidence

ORD record
ord-513456c83175435f8d1c6821090db18f
Source dataset
uspto-grants-2011_04
Patent number
US07928253B2

Reaction notes

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