Water → HCID 58372832, compound

HRID 656752Notes

Reaction equation

HRID 656752 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1)C(OC)=O.[Cl-].[Li+].O>CS(C)=O.O>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 583727782-(3-Benzyloxy-5-chloro-phenyl)-malonic acid dimethyl ester

Product 1

HCID 58372832HCID 58372832, compound

Reagents, catalysts & solvents 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(3-benzyloxy-5-chloro-phenyl)-malonic acid dimethyl ester (21 g, 60.2 mmol) and lithium chloride (3.06 g, 72.2 mmol) in DMSO:H2O (10:1; 200 mL) was stirred at 150° C. for 5 hours. After cooling to room temperature, H2O (500 mL) was added, and the mixture was extracted with EtOAc:hexanes (1:10; 1.5 L total) to give the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc:hexanes (1:10; 1.5 L total)

Sources & evidence

ORD record
ord-6ae15aab3dc9497980fbc108a0125117
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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