Triphenylphosphine → HCID 117760003, compound

HRID 1049461Notes

Reaction equation

HRID 1049461 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[F:21])[CH:9]=[CH:10][C:11]=1[OH:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:43]1([CH:46]([C:53]2[CH:58]=[CH:57][CH:56]=[C:55]([CH2:59]O)[CH:54]=2)[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:45][CH2:44]1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH:43]1([CH:46]([C:53]2[CH:58]=[CH:57][CH:56]=[C:55]([CH2:59][O:12][C:11]3[CH:10]=[CH:9][C:8]([C:13]4[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=4[F:21])=[CH:7][C:6]=3[CH2:5][CH2:4][CH2:3][C:2]([CH3:23])([CH3:22])[CH3:1])[CH:54]=2)[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:45][CH2:44]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoateHCID 117760173HCID 117760173, compound

Product 1

HCID 117760003HCID 117760003, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4,4-dimethylpentyl)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-4-ol (280 mg) in THF (5.0 mL) were added triphenylphosphine (348 mg), ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (330 mg) and a 40% solution of diethyl azodicarboxylate in toluene (600 μL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (380 mg) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-953d9b36950d456fb5147817378ef186
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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