Ethyl orthoformate → HCID 69591221, compound

HRID 2216299Notes

Reaction equation

HRID 2216299 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2].[CH:18](OCC)(OCC)[O:19][CH2:20][CH3:21]>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4](=[O:17])[C:5]([S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:7])=[O:8])=[CH:18][O:19][CH2:20][CH3:21])[CH3:2]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 14823722-[(4-Methoxyphenyl)sulfonyl]acetic acid ethyl ester

Product 1

HCID 69591221HCID 69591221, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of (4-methoxy-benzenesulfonyl)-acetic acid ethyl ester (8.3 g, 32 mmol) and triethyl orthoformate (16 mL, 96 mmol) in acetic anhydride (20 mL) was refluxed under N2 for 16 h. Solvents were removed by distillation (keep the temperature of oil bath below 180° C.). The residue was purified by chromatography on silica gel (1:1 ethyl acetate/hexanes) to provide the desired product as a mixture of isomers (a mixture of trans- and cis-isomers, 5.3 g, 53%) as a light yellow oil.

Workup

  1. temperaturewas refluxed under N2 for 16 h
  2. customSolvents were removed by distillation (
  3. custombelow 180° C.
  4. customThe residue was purified by chromatography on silica gel (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-95368a16fc234f4ebc2e5958c831e1af
Source dataset
uspto-grants-2006_09
Patent number
US07112585B2

Reaction notes

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