Triphenylphosphine → HCID 87426500, compound

HRID 623509Notes

Reaction equation

HRID 623509 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[F:13][CH:14]([F:17])[CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:13][CH:14]([F:17])[CH2:15][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1361872,2-Difluoroethan-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11240684Methyl 4-hydroxy-3-methylbenzoate

Product 1

HCID 87426500HCID 87426500, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-hydroxy-3-methylbenzoate (1.5 g, 9.0 mmol), 2,2-difluoroethanol (0.90 g, 10.8 mmol), triphenylphosphine (3.6 g, 13.5 mmol) in THF (40 mL) is added dropwise diethyl azodicarboxylate (4.9 mL, 10.8 mmol, 40% solution in toluene) at 0° C. The mixture is stirred at room temperature for 30 minutes, and then at 60° C. for 2 hours. After cooled to room temperature, the mixture is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (18:1) to give 1.9 g (90% yield) of the title compound as a white solid.

Workup

  1. waitat 60° C. for 2 hours
  2. temperatureAfter cooled to room temperature
  3. concentrationthe mixture is concentrated under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (18:1)

Sources & evidence

ORD record
ord-f84b786bb3b04a468e4ffc19b0a61162
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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