Ozone → 2-(4-Chloro-2-indanyl) ethanol

HRID 1646547ノート

反応式

HRID 1646547 の反応式
[CH2:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:13])[CH2:5]1)[CH:2]=C.[O:14]=[O+][O-]>CO.ClCCl>[Cl:13][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH2:12][CH:4]([CH2:1][CH2:2][OH:14])[CH2:5]2

参加物

5

反応物 2

HCID 24823OzoneHCID 19801146HCID 19801146、化合物

生成物 1

HCID 543631012-(4-Chloro-2-indanyl) ethanol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Amalgamated zinc (prepared from zinc powder (6 g), mercuric chloride (0.6 g)) was heated under reflux for 7 hours with 2-allyl-4-chloro-indan-1-one (3 g), toluene (20 ml), conc. hydrochloric acid (20 ml), water (8 ml) and acetic acid (2 ml). Upon cooling conventional work-up gave a crude product which was purified by chromatography (silica/hexane) to give a 2-allyl-4-chloroindane (1.8 g). 2-Allyl-4-chloroindane (0.8 g) in dry methanol (10 ml) and dry dichloromethane (2 ml) was reacted at -35° with ozone until the blue colour persisted. After purging with nitrogen the solution was stirred 16 hours with dimethyl sulphide (2.58 g). The volatiles were removed and the residue taken up in tetrahydrofuran (10 ml) and heated under reflux with 4-toluenesulphonic acid (30 mg) and water (circa 0.5 ml) for 2 hours. After conventional work up the product, 2-(4-chloro-2-indanyl) ethanol, was obtained as a yellow oil (0.8 g).

後処理

  1. customAfter purging with nitrogen the solution
  2. customThe volatiles were removed
  3. temperatureheated
  4. temperatureunder reflux with 4-toluenesulphonic acid (30 mg) and water (circa 0.5 ml) for 2 hours

出典と根拠

ORDレコード
ord-a2b0c7514c7e45569e60cd63199b343b
出典データセット
uspto-grants-1993_01
特許番号
US05180737

反応ノート

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