Triphenylphosphine → HCID 117760221, compound

HRID 709840Notes

Reaction equation

HRID 709840 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7][OH:8])=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:38]1([CH:41]([C:47]2[CH:52]=[CH:51][CH:50]=[C:49](O)[CH:48]=2)[CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH2:40][CH2:39]1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([CH2:7][O:8][C:51]2[CH:52]=[C:47]([CH:41]([CH:38]3[CH2:39][CH2:40]3)[CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:48]=[CH:49][CH:50]=2)=[N:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57706598Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoateHCID 90153637HCID 90153637, compound

Product 1

HCID 117760221HCID 117760221, compoundYield 22.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-bromo-4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)methanol (300 mg) in THF (15 ml) were added triphenylphosphine (349 mg), methyl 3-cyclopropyl-3-(3-hydroxyphenyl)propanoate (293 mg), and a 40% solution of diethyl azodicarboxylate in toluene (520 μL), and the mixture was stirred at room temperature for 30 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 (110 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-c64e3287057e4083b62b4164dc3bd29a
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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