Methanol → (+)-trans-1-t-Butyldimethylsilyloxymethyl-4-oxo-2-phenylcyclopentane

HRID 1634270Notes

Reaction equation

HRID 1634270 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C:13](=C)[CH2:12][C@H:11]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[OH:23]>>[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C:13](=[O:23])[CH2:12][C@H:11]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 18686191(+-)-trans-1-t-Butyldimethylsilyloxymethyl-4-methylene-2-phenylcyclopentane

Product 1

HCID 18686192(+)-trans-1-t-Butyldimethylsilyloxymethyl-4-oxo-2-phenylcyclopentane

Procedure

Into a solution of (+−)-trans-1-t-butyldimethylsilyloxymethyl-4-methylene-2-phenylcyclopentane from Step B1 (2.2 g, 7.3 mmol) in methanol (100 mL) cooled in a dry ice/acetone bath was bubbled ozone until the blue color persisted. The excess ozone was removed with a stream of nitrogen and then dimethylsulfide (5 mL) was added. After 10 min, the bath was removed and the reaction was allowed to warm to rt over 2 h. The volatiles were removed in vacuo and the residue was purified by FC (15-30% ethyl acetate in hexanes) to give the title compound (1.9 g) which was the same as in Method A.

Workup

  1. customwas bubbled ozone until the blue color
  2. customThe excess ozone was removed with a stream of nitrogen
  3. additiondimethylsulfide (5 mL) was added
  4. customthe bath was removed
  5. customThe volatiles were removed in vacuo
  6. customthe residue was purified by FC (15-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-752c839283fa4b6e8bfa4fcfd035f5c8
Source dataset
uspto-grants-2003_01
Patent number
US06506777B1

Reaction notes

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