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Thionyl Chloride → 1-[(1R,2R)-3-chloro-1-ethyl-2-methylpropyl]-3-(phenylmethoxy)benzene

HRID 1771018
ノート
印刷プレビュー

反応式

HRID 1771018 の反応式
[CH2:1]([C@@H:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[C@@H:4]([CH3:7])[CH2:5]O)[CH3:2].S(Cl)([Cl:24])=O>ClCCl.CN(C)C=O>[Cl:24][CH2:5][C@H:4]([CH3:7])[C@H:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[CH2:1][CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 60164839(betaR,gammaR)-gamma-ethyl-beta-methyl-3-(phenylmethoxy)benzenepropanol

生成物 1

HCID 601648431-[(1R,2R)-3-chloro-1-ethyl-2-methylpropyl]-3-(phenylmethoxy)benzene収率 90%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

The product of Example 32 (2.6 g, 9 mmol) was dissolved in dichloromethane, the mixture was cooled in an ice-water bath, then N, N-dimethylformamide (2 drops) was added and thionyl chloride (0.64 mL, 10 mmol) was added dropwise, after the addition was complete, the reaction was conducted under reflux for 6 hours and quenched by adding water. After the reaction solution was separated, the aqueous phase was extracted with dichloromethane three times, and the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the target compound 2.4 g, yield: 90%.

後処理

  1. temperaturethe mixture was cooled in an ice-water bath
  2. additionafter the addition
  3. temperatureunder reflux for 6 hours
  4. customquenched
  5. additionby adding water
  6. customAfter the reaction solution was separated
  7. extractionthe aqueous phase was extracted with dichloromethane three times
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-12a5110d13ad40308a3d6330aedcb1b5
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09249084B2

反応ノート

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