Acetic Acid → 3,3a,4,5,6,6a-hexahydro-2H-pentalen-1-one

HRID 462771노트

반응식

HRID 462771 반응식
COC(CCC/C=[C:9]1/[C:10](=[O:17])[CH:11]2[CH:15]([CH2:16]/1)[CH2:14][CH2:13][CH2:12]2)=O.[OH-].[Li+].C(O)(=O)C>CO>[CH:11]12[CH2:12][CH2:13][CH2:14][CH:15]1[CH2:16][CH2:9][C:10]2=[O:17]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 867400973-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one

생성물 1

HCID 1406313,3a,4,5,6,6a-hexahydro-2H-pentalen-1-one수율 148%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
10 °C

실험 절차

A stirred solution of 6-[(E)-(mixture of 3β and 3β)-hydroxyoct-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one (90 mg), prepared as described in Example 4 and predominantly in the 6β-configuration, otherwise known as (±)-methyl(5E,13E)-(9S),[mixture of (15R) and (15S)]-6a-oxo-6,9-methano-15-hydroxyprosta-5,13-dienoate, in methanol (2 ml) at 5° C. was treated with aqueous lithium hydroxide solution (1.5 ml; 1.0N). The resulting solution was stirred for 3.3 hours at 10° C. and was then treated with glacial acetic acid (0.1 ml). The methanol was removed in vacuo and the residue was diluted with ethyl acetate (10 ml), washed with hydrochloric acid (2N), then with water, and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate and concentrated in vacuo, to give 3-[(E)-4-carboxybutylidene]-6-[(E)-(mixture of 3α and 3β)-hydroxyoct-1-enyl]bicyclo[3,3,0]octan-2-one (70.0 mg), thought to be in the 6β-configuration, otherwise known as (±)-(5E,13E)-(9S),[mixture of (15R) and (15S)]-6a-oxo-6,9-methano-15-hydroxyprosta-5,13-dienoic acid [NMR in deuterochloroform: multiplets at 6.6, 5.5, 4.8-3.7, 3.0-1.1, 1.1-0.7 p.p.m⟧

후처리

  1. customThe methanol was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate (10 ml)
  3. washwashed with hydrochloric acid (2N)
  4. dry with materialwith water, and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8444afcb6dba4559979b26b713a2d9a1
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04517202

반응 노트

불러오는 중…