Triphenylphosphine → HCID 57804302, compound

HRID 2103432Notes

Reaction equation

HRID 2103432 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10][OH:11])[CH2:2][CH2:3][CH3:4].[CH3:22][O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][C:26]=1[Cl:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[CH3:22][O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:11][CH2:10][C:9]2[S:8][C:7]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:14][CH:13]=3)=[N:6][C:5]=2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:27][C:26]=1[Cl:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl esterHCID 58934102HCID 58934102, compound

Product 1

HCID 57804302HCID 57804302, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of [4-butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol (1.0 g, 3.17 mmol), 2-chloro-4-hydroxy-benzoic acid methyl ester (592 mg, 3.17 mmol) and triphenylphosphine (832 mg, 3.17 mmol) in dichloromethane add diethyl azodicarboxylate (0.567 mL, 3.17 mmol). Stir the reaction mixture for 2 hours while allowing it to warm to room temperature. Remove the solvent under reduced pressure and purify the residue by flash chromatography on silica gel to give 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-benzoic acid methyl ester (600 mg).

Workup

  1. customRemove the solvent under reduced pressure
  2. custompurify the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3c358532a07f4922b3bb51200415933e
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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