Triphenylphosphine → [2-(3-Ethoxycarbonyl-2-phenylpropyl)-1,3-oxazol-4-yl]methyltriphenylphosphonium bromide

HRID 989901Notes

Reaction equation

HRID 989901 reaction equation
[Br:1][CH2:2][C:3]1[N:4]=[C:5]([CH2:8][CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:6][CH:7]=1.[CH:22]1[CH:27]=[CH:26][C:25]([P:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:23]=1>CC#N>[Br-:1].[CH2:14]([O:13][C:11]([CH2:10][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:5]1[O:6][CH:7]=[C:3]([CH2:2][P+:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:25]2[CH:24]=[CH:23][CH:22]=[CH:27][CH:26]=2)[N:4]=1)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 23389064Ethyl (+/-)-4-(4-bromomethyl-1,3-oxazol-2-yl)-3-phenylbutanoate

Product 1

HCID 18419548[2-(3-Ethoxycarbonyl-2-phenylpropyl)-1,3-oxazol-4-yl]methyltriphenylphosphonium bromideYield 95.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl (±)-4-(4-bromomethyl-1,3-oxazol-2-yl)-3-phenylbutanoate (1.0 g, 2.84 mmole) and PPh3 (745 mg, 2.84 mmole) in dry CH3CN (10 mL) was heated at reflux under N2. After 3 hr, the mixture was cooled to RT and concentrated under reduced pressure. The residue was triturated with Et2O (10 mL) to give the title compound (1.66 g, 95%) as a white powder: MS (ES) m/e 535 (M+H)+.

Workup

  1. temperatureat reflux under N2
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with Et2O (10 mL)

Sources & evidence

ORD record
ord-77f61c63de6a4ed0b77b4e4c07a242e2
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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