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

HRID 1856145ノート

反応式

HRID 1856145 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒HCID 7918Acetic Anhydride溶媒

実験手順

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 mp: 44°-45.5° C., [α]D25 -85.6° (c=2.0; CHCl3).

後処理

  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

出典と根拠

ORDレコード
ord-c2ef7354410f4fdf9b8470d9b39e6faf
出典データセット
uspto-grants-1980_08
特許番号
US04218402

反応ノート

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