3-Methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol → a Methyl jasmonate

HRID 1732438

반응식

HRID 1732438 반응식
[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([OH:11])[CH:7]1[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16])=[O:4]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH:7]1[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16])=[O:4]

참가 물질

3

반응물 1

HCID 100595943-Methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

생성물 1

HCID 5319693a Methyl jasmonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
18 °C

실험 절차

A 150 mg quantity of 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol is dissolved in 10 ml of methylene chloride. A 2 ml quantity of chromic acid solution of 2 M concentration is added dropwise to the solution. The mixture is stirred at about 18° C. for 12 hours and thereafter extracted with ethyl acetate. The extract is washed with aqueous solution of sodium chloride, dried and concentrated. The residue is purified with a silica gel column and distilled in a vacuum, affording 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanone (compound (4), R2 =CH3) in a yield of 88%, b.p. 92°-96° C./2.7 mm Hg.

후처리

  1. concentrationA 2 ml quantity of chromic acid solution of 2 M concentration
  2. additionis added dropwise to the solution
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with aqueous solution of sodium chloride
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is purified with a silica gel column
  8. distillationdistilled in a vacuum

출처 및 근거

ORD 기록
ord-067fa63bb80d4e94acebb1b91ba3278b
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04237308

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