Triphenylphosphine → 3-[2-(2-Fluoro-5-methyl-phenyl)-ethoxy]-4-methoxy-benzoic Acid Methyl Ester

HRID 1918277Notes

Reaction equation

HRID 1918277 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][CH2:10][OH:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][O:32][C:33](=[O:43])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36](O)[CH:35]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:31][O:32][C:33](=[O:43])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:11][CH2:10][CH2:9][C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[F:1])[CH:35]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 5363146Diisopropyl azodicarboxylateHCID 583183722-(2-Fluoro-5-methyl-phenyl)-ethanol

Product 1

HCID 671704563-[2-(2-Fluoro-5-methyl-phenyl)-ethoxy]-4-methoxy-benzoic Acid Methyl EsterYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Fluoro-5-methyl-phenyl)-ethanol (508 mg, 3.29 mmol) was dissolved in THF (23 ml). Triphenylphosphine (1.08 g, 4.12 mmol) and 3-hydroxy-4-methoxy-benzoic acid methyl ester (500 mg, 2.75 mmol) were added, the mixture was cooled in an ice bath, and DIAD (832 mg, 4.12 mmol) was added slowly with stirring. The ice bath was removed and stirring was continued overnight at room temperature. The volatiles were evaporated in vacuo, and the residue was purified by RP HPLC (water/ACN gradient) to give 530 mg of the title compound.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe ice bath was removed
  3. stirringstirring
  4. customThe volatiles were evaporated in vacuo
  5. customthe residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-a18d6fa229bf42acaf4f2ef904d1fcb7
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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