Methanesulfonyl chloride → 3-(3-Benzyloxy-phenyl)-2-methoxy-acrylic acid methyl ester

HRID 459169Notes

Reaction equation

HRID 459169 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([O:21][CH3:22])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)O.S(Cl)(C)(=O)=O>CN(C1C=CN=CC=1)C.ClCCl.CCOCC>[CH3:1][O:2][C:3](=[O:23])[C:4]([O:21][CH3:22])=[CH:5][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 588226943-(3-Benzyloxy-phenyl)-3-hydroxy-2-methoxy-propionic acid methyl ester

Product 1

HCID 694217553-(3-Benzyloxy-phenyl)-2-methoxy-acrylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-Benzyloxy-phenyl)-3-hydroxy-2-methoxy-propionic acid methyl ester (1 eq), mesylchloride (1 eq) triethylamine (4 eq) and a catalytic amount of DMAP (0.1 eq) in dichloromethane was stirred at room temperature overnight. The Reaction mixture was diluted with ether and washed with HCl 1N. Dried and concentrated in vacuo to give a residue which was chromatographed in silica gel to yield the title compound.

Workup

  1. washwashed with HCl 1N
  2. customDried
  3. concentrationconcentrated in vacuo
  4. customto give a residue which
  5. customwas chromatographed in silica gel

Sources & evidence

ORD record
ord-e971701bbd7a4eb7bc6f4368de2f246a
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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