(2-Oxooxolan-3-yl)(triphenyl)phosphanium bromide → 2(3H)-Furanone, 3-(triphenylphosphoranylidene)-

HRID 973879Notes

Reaction equation

HRID 973879 reaction equation
[Br-].[O:2]=[C:3]1[CH:7]([P+:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][O:4]1>O>[O:2]=[C:3]1[C:7](=[P:8]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5][O:4]1

Participants

3

Reactant 1

HCID 19988396(2-Oxooxolan-3-yl)(triphenyl)phosphanium bromide

Product 1

HCID 971112(3H)-Furanone, 3-(triphenylphosphoranylidene)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Oxotetrahydrofuran-3-yltriphenylphosphonium bromide (1.717 g) was dissolved in water (20 mls) and the solution filtered through kieselguhr. The pH was adjusted to 7.5 with 5M sodium hydroxide. The greyish precipitate was filtered off, washed with 50% ether/acetone and dried, to give the title compound as an off white solid, (0.77 g, 55%), (Found; M+, 346.1124. C22H19O2P requires M, 346.1123); νmax (CH2Cl2) 1645, 1480(w), 1430(w), 1365(w) and 1315(w)cm-1 ; δH (CDCl3) 2.62 (2H, t, 7Hz), 4.27 (2H, t, J 7Hz) and 7.3-7.9 (15H, m).

Workup

  1. filtrationthe solution filtered through kieselguhr
  2. filtrationThe greyish precipitate was filtered off
  3. washwashed with 50% ether/acetone
  4. customdried

Sources & evidence

ORD record
ord-32e461011d0c405695236975e1d2040f
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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