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

HRID 1771018Notes

Reaction equation

HRID 1771018 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-12a5110d13ad40308a3d6330aedcb1b5
Source dataset
uspto-grants-2016_02
Patent number
US09249084B2

Reaction notes

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