Methanol → (+)-trans-3-Hydroxymethyl-4-phenylcyclopentan-1-one

HRID 1357959Notes

Reaction equation

HRID 1357959 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][C:6](=C)[CH2:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[OH:16]>>[OH:1][CH2:2][C@@H:3]1[CH2:7][C:6](=[O:16])[CH2:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 18686190(+-)-trans-1-Hydroxymethyl-4-methylene-2-phenylcyclopentane

Product 1

HCID 53754795(+)-trans-3-Hydroxymethyl-4-phenylcyclopentan-1-one

Procedure

Into a solution of (+−)-trans-1-hydroxymethyl-4-methylene-2-phenylcyclopentane from Step B (22.7 g, 121 mmol) in methanol (300 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 (25 mL) was added. After 30 min, the bath was removed and the reaction was allowed to warm to rt over 16 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 (22.1 g).

Workup

  1. customwas bubbled ozone until the blue color
  2. customThe excess ozone was removed with a stream of nitrogen
  3. additiondimethylsulfide (25 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-35533d2f27ca4aac9acc2c95dd2cce8f
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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