Methanesulfonyl chloride → 4-Benzyloxy-3-methyl-phenyl-2-methoxy-acrylic acid ethyl ester

HRID 459180Notes

Reaction equation

HRID 459180 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([O:23][CH3:24])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([CH3:22])[CH:9]=1)O)[CH3:2].S(Cl)(C)(=O)=O>CN(C1C=CN=CC=1)C.ClCCl.CCOCC>[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:23][CH3:24])=[CH:6][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:10]([CH3:22])[CH:9]=1)[CH3:2]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 694224223-(4-Benzyloxy-3-methyl-phenyl)-3-hydroxy-2-methoxy-propionic acid ethyl ester

Product 1

HCID 694952094-Benzyloxy-3-methyl-phenyl-2-methoxy-acrylic acid ethyl ester

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 3-(4-Benzyloxy-3-methyl-phenyl)-3-hydroxy-2-methoxy-propionic acid ethyl 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 over night. 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-87afeabfc67d4f01aa96f5e6621454f6
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

Loading…