Acetic Acid → 3-Methoxycarbonylmethyl-2-methoxycarbonyl-2-(2-pentynyl)-cyclopentanol

HRID 46549노트

반응식

HRID 46549 반응식
[C:1]([O:5][C:6]([C:8]1([CH2:19][C:20]#[C:21][CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])(C)(C)C.[BH4-].[Na+].C(O)(=O)C>CO>[CH3:18][O:17][C:15]([CH2:14][CH:9]1[CH2:10][CH2:11][CH:12]([OH:13])[C:8]1([C:6]([O:5][CH3:1])=[O:7])[CH2:19][C:20]#[C:21][CH2:22][CH3:23])=[O:16]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 203065655-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone2회

생성물 1

HCID 203875833-Methoxycarbonylmethyl-2-methoxycarbonyl-2-(2-pentynyl)-cyclopentanol

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A 5 q quantity of 5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (2-a)) and 1.35 g of sodium borohydride are dissolved in 200 ml of methanol, and the solution is refluxed in a nitrogen atmosphere for one hour. The reaction mixture is cooled to room temperature, and about 30 ml of acetic acid is added to the mixture. The resulting mixture is stirred for 30 minutes and thereafter concentrated in a vacuum. The residue is dissolved in a mixture of benzene and ethyl acetate, and the solution is purified with a silica gel column. After removing the solvent from the product, the product is distilled in a vacuum, affording 3-methoxycarbonylmethyl-2-methoxycarbonyl-2-(2-pentynyl)-cyclopentanol (compound (1-a), R1 =R2 +CH3) in a yield of 92.5%, b.p. 70-75° C./0.005 mm Hg.

후처리

  1. temperaturethe solution is refluxed in a nitrogen atmosphere for one hour
  2. concentrationconcentrated in a vacuum
  3. dissolutionThe residue is dissolved in a mixture of benzene and ethyl acetate
  4. customthe solution is purified with a silica gel column
  5. customAfter removing the solvent from the product
  6. distillationthe product is distilled in a vacuum

출처 및 근거

ORD 기록
ord-6795ea32d15d49fb96b0c27728a17d79
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04173707

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