Thionyl Chloride → HCID 21920046, compound

HRID 1823039Notes

Reaction equation

HRID 1823039 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH:18]([CH2:20]O)[CH2:17][C:16]2=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH:18]([CH2:20][Cl:25])[CH2:17][C:16]2=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10447336(RS)-1-(4-Benzyloxy-phenyl)-4-hydroxymethyl-pyrrolidin-2-one

Product 1

HCID 21920046HCID 21920046, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

740 mg (2.49 mmol) (RS)-1-(4-benzyloxy-phenyl)-4-hydroxymethyl-pyrrolidin-2-one is dissolved in 20 ml toluene. 1.08 ml (14.9 mmol) thionyl chloride is added and the mixture refluxed for 6 hours. Evaporation and chromatography (silica gel, n-hexane/ethyl acetate 1:1) yields 123 mg (16%) of a brownish semisolid. MS: m/e=315.2 (M+).

Workup

  1. temperaturethe mixture refluxed for 6 hours
  2. customEvaporation and chromatography (silica gel, n-hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-7170a89382b04457b1801bf556ad56fc
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

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