Triphenylphosphine → HCID 19745625, compound

HRID 2253722Notes

Reaction equation

HRID 2253722 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]([OH:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[F:14][C@@H:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:1][C:2]1[C:11]([F:12])=[C:10]([O:13][CH2:16][CH:15]([F:14])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11137325(S)-2-fluorooctane-1-olHCID 22999141HCID 22999141, compound

Product 1

HCID 19745625HCID 19745625, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.05 mol of methyl 2,3-difluoro-4-hydroxybenzoate, 0.05 mol of (S)-2-fluorooctan-1-ol and 0.06 mol of triphenylphosphine are dissolved in 125 ml of tetrahydrofuran, and 0.06 mol of diethyl azodicarboxylate is added dropwise with stirring and ice cooling. The mixture is allowed to warm to room temperature and is stirred for a further 8 hours. The solvent is then removed by distillation, and the methyl 2,3-difluoro-4-(2-fluorooctyloxy)benzoate is purified by column chromatography. 2,3-Difluoro-4-(2-fluorooctyloxy)benzoic acid is obtained therefrom by hydrolysis using aqueous/alcoholic potassium hydroxide solution.

Workup

  1. stirringis stirred for a further 8 hours
  2. customThe solvent is then removed by distillation
  3. customthe methyl 2,3-difluoro-4-(2-fluorooctyloxy)benzoate is purified by column chromatography

Sources & evidence

ORD record
ord-e59959a2d58342c3895671ed9936dd2c
Source dataset
uspto-grants-1993_08
Patent number
US05232624

Reaction notes

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