Triphenylphosphine → HCID 178520709, compound

HRID 1417929Notes

Reaction equation

HRID 1417929 reaction equation
[Br:1][CH2:2][CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1>[Br-:1].[CH2:8]([O:7][C:5]([CH2:4][CH:3]=[CH:2][PH:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 54298885Benzyl 4-bromo-but-2-enate

Product 1

HCID 178520709HCID 178520709, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of benzyl 4-bromo-but-2-enate (430 mg, 1.68 mmol) and triphenylphosphine (661 mg, 2.52 mmol) in benzene (3 ml) was stirred at room temperature under nitrogen for 20 hours. The resulting white solid was collected through filtration and washed with benzene (3×2 ml), and dried at 100° C. under vacuum to give the title compound (510 mg, 59% yield). 1H NMR (CD3OD): δppm 4.60 (2H, m, slowly disappeared due to deuterium exchange), 5.13 (2H, s), 6.16 (1H, dd, J1=15.3 Hz, J2=1.1 Hz), 6.81 (1H, m), 7.33 (5H, m), 7.78 (12 H, m), 7.90 (3H, m). 13C NMR (CD3OD): δppm 67.6 (t), 68.1 (t), 118.3 (s), 118.8 (s), 119.4 (s), 120.0 (s), 129.3 (d), 129.4 (d), 129.5 (d), 129.6 (d), 129.7 (d), 131.4 (d), 131.5 (d), 131.7 (d), 134.7 (d), 134.85 (d), 134.94 (d), 135.1 (d), 135.2 (d), 135.3 (d), 136.5 (d), 136.6 (d), 136.69 (d), 136.73 (d), 155.7 (s); 165.8 (s).

Workup

  1. filtrationThe resulting white solid was collected through filtration
  2. washwashed with benzene (3×2 ml)
  3. customdried at 100° C. under vacuum

Sources & evidence

ORD record
ord-9830221b11fa4aef9e2400df4785e888
Source dataset
uspto-grants-1999_03
Patent number
US05879894

Reaction notes

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