Phenylsilane → 2-Methyl-6-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-4-propoxy-benzoic acid

HRID 644015Notes

Reaction equation

HRID 644015 reaction equation
C([O:4][C:5](=[O:40])[C:6]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])=[CH:16][CH:15]=2)=[CH:10][C:9]([O:35][CH2:36][CH2:37][CH3:38])=[CH:8][C:7]=1[CH3:39])C=C.C1([SiH3])C=CC=CC=1>C(Cl)Cl>[CH3:39][C:7]1[CH:8]=[C:9]([O:35][CH2:36][CH2:37][CH3:38])[CH:10]=[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])=[CH:16][CH:15]=2)[C:6]=1[C:5]([OH:40])=[O:4]

Participants

4

Reactant 2

HCID 12752PhenylsilaneHCID 685796982-Methyl-6-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}4-propoxy-benzoic acid allyl ester

Product 1

HCID 592632932-Methyl-6-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-4-propoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the title D compound, 2-methyl-6-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-4-propoxy-benzoic acid allyl ester (620 mg, 1.16 mmol), tetrakis-(triphenyl-phosphine)palladium(0) (27 mg, 0.02 equivalents), and phenyl silane (252 mg, 2.33 mmol) in DCM (15 mL) is stirred at RT for 4 h. The mixture is concentrated under vacuum, and the residue is chromatographed on silica gel using a solvent mixture consisting of 0.5% formic acid and 20% ethyl acetate in hexane as the eluent to afford 2-methyl-6-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-4-propoxy-benzoic acid as a white foam: m.p. 50-52° C.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. customthe residue is chromatographed on silica gel using a solvent mixture

Sources & evidence

ORD record
ord-5dda04c1ca6f4cfeb8db3d1b12671dfd
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

Loading…