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

HRID 2301764Notes

Reaction equation

HRID 2301764 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 C (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).

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-1f1e1ae61fcb4fe4a4f47fe27a1bfe8d
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

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