p-Toluenesulfonic acid monohydrate → (1R,6S)- 4,7,7-Trimethyl-3-oxabicyclo[4.1.0]hept-4-en-2-one

HRID 263160노트

반응식

HRID 263160 반응식
[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH2:5][C:6](=O)[CH3:7])[C@H:3]1[C:9]([OH:11])=[O:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC(=O)C)(=O)C.C1C=CC=CC=1.CCOCC>[CH3:7][C:6]1[O:10][C:9](=[O:11])[C@@H:3]2[C@H:4]([CH:5]=1)[C:2]2([CH3:12])[CH3:1]

참가 물질

6

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 10899111(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropanecarboxylic acid

생성물 1

HCID 11789393(1R,6S)- 4,7,7-Trimethyl-3-oxabicyclo[4.1.0]hept-4-en-2-one수율 93%

시약·촉매·용매 3

HCID 241Benzene용매HCID 3283Diethyl Ether용매HCID 7918Acetic Anhydride용매

실험 절차

A solution of 20 g (0.17 mol) of (1R,cis)-2,2-dimethyl-3-(2-oxopropyl)cyclopropane-1-carboxylic acid and 3 g (0.016 mol) of p-toluenesulfonic acid monohydrate in 93 ml of acetic anhydride and 150 ml of benzene was stirred for 30 minutes at 10°-20° C. The slightly darkened mixture was diluted with ether and washed with ice cold saturated sodium bicarbonate solution until the washings were basic. The organic phase was dried over anhydrous magnesium sulfate and decolorized with charcoal. The solvent was evaporated in vacuo to give 24 g (93%) of the product as a tan solid. Recrystallization from pentane gave a white solid (III) mp 44°-45.5° C., [α]D25 -85.6° (c, 2.0; CHCl3).

후처리

  1. washwashed with ice cold saturated sodium bicarbonate solution until the washings
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-a8a7b92029f74fb690aa2219bc0239e8
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04156692

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