Triphenylphosphine → HCID 23136285, compound

HRID 1678589Notes

Reaction equation

HRID 1678589 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[O:16]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH2:29][C:26]1[CH:27]=[CH:28][C:23]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 826195(4-Phenoxyphenyl)methanolHCID 3023769Ethyl 3-(3-fluoro-4-hydroxyphenyl)propionate

Product 1

HCID 23136285HCID 23136285, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ice-cooled ethyl 3-(3-fluoro-4-hydroxyphenyl)propanoate (0.19 g, 0.88 mmol), (4-phenoxyphenyl)methanol (0.12 g, 0.58 mmol) and triphenylphosphine (0.23 g, 0.88 mmol) in tetrahydrofuran (5 mL) was added dropwise diethyl azodicarboxylate (a 40% solution in toluene, 0.40 mL, 0.88 mmol), and the mixture was stirred at room temperature for 4 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=8:2) to give the title compound (0.16 g, yield 71%) as an oily matter.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=8:2)

Sources & evidence

ORD record
ord-c85ee14e54504e02b5691f8d4725a689
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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