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

HRID 1771018
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HRID 1771018 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-12a5110d13ad40308a3d6330aedcb1b5
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249084B2

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