Triphenylphosphine → Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)oxy)methyl)phenyl)propanoate

HRID 1049409Notes

Reaction equation

HRID 1049409 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19].[CH:22]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]O)[CH:33]=2)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24][CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH:22]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][O:16][C:13]3[CH:14]=[CH:15][C:10]([C:3]4[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=4[F:1])=[C:11]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=3)[CH:33]=2)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1177596322'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-olHCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate

Product 1

HCID 117759943Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)oxy)methyl)phenyl)propanoateYield 56.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-ol (388 mg), ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (261 mg) and triphenylphosphine (413 mg) in THF (10 mL) was added a 40% solution of diethyl azodicarboxylate in toluene (620 μL) at 0° C., and the mixture was stirred at room temperature for 70 min. 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 (310 mg) as a pale-yellow 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-1fefb9cbc18d48569fe7c6fce7f3aaff
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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