3-Phenylpropyl triphenylphosphonium bromide → 5-(4-Bromo-phenyl)-3-methyl-4-(4-phenyl-but-1-enyl)-isoxazole

HRID 1183268Notes

Reaction equation

[Br-].[C:2]1([CH2:8][CH2:9][CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Br:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[O:46][N:45]=[C:44]([CH3:47])[C:43]=2[CH:48]=O)=[CH:38][CH:37]=1>C1COCC1.Cl>[Br:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[O:46][N:45]=[C:44]([CH3:47])[C:43]=2[CH:48]=[CH:10][CH2:9][CH2:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:40][CH:41]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3-phenylpropyl)triphenylphosphonium bromide (0.956 g, 2.07 mmol) in THF (5 mL) at −78° C. was slowly added n-butyllithium (2.5M in hexanes; 0.83 mL, 2.07 mmol), and the mixture was stirred for 15 minutes. 5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (0.500 g, 1.88 mmol) in THF (3 mL) was added, and the reaction was warmed to 0° C. and stirred for 1 hour. The solution was diluted with 1N aqueous HCl and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, decanted, and concentrated. The residue was purified by silica gel chromatography (0-20% EtOAc in hexanes) to give the title compound.

Workup

customat −78° C.
stirringstirred for 1 hour
extractionextracted twice with EtOAc
dry with materialThe combined organic layers were dried over Na2SO4
customdecanted
concentrationconcentrated
customThe residue was purified by silica gel chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-e5201b4b14a04a45b8f126c899c9d8da
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664220B2

Reaction notes

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