Triphenylphosphine → HCID 89581019, compound

HRID 1501243Notes

Reaction equation

HRID 1501243 reaction equation
[OH:1][CH:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)[CH3:3].[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[O:1][CH:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:13])=[O:9])=[CH:6][CH:5]=1)[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1230512,4-DifluorophenolHCID 5363146Diisopropyl azodicarboxylateHCID 22731454HCID 22731454, compound

Product 1

HCID 89581019HCID 89581019, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 4-(1-hydroxyethyl)benzoate (300 mg. 1.67 mmol) in tetrahydrofuran (80 mL) was added triphenylphosphine (570 mg, 2.2 mmol) and 2,4-difluorophenol (159 mg, 1.67 mmol), the mixture was stirred for 30 minutes at room temperature, then diisopropylazodicarboxylate (568.3 mg, 2.2 mmol) was added dropwise to the solution at 0° C. The mixture was stirred at room temperature for 12 hours. Then the mixture was concentrated and the residue was purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1) to give methyl 4-(1-(2,4-difluorophenoxy)ethyl)benzoate (151 mg, 33%) as oil. 1H-NMR (300 MHz, CD3OD) δ 8.03 (d, J=8.1 Hz, 2H), 7.460 (d, J=8.1 Hz, 2H), 6.86-6.72 (m, 3H), 5.29 (q, 1H), 3.91 (s, 3H), 1.67 (d, J=6.3 Hz, 2H).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. concentrationThen the mixture was concentrated
  3. customthe residue was purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-49415983711448ffb3ee7c12b4f04c2b
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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