Triphenylphosphine → HCID 67923954, compound

HRID 973867Notes

Reaction equation

HRID 973867 reaction equation
[Br:1]C1OCC=C1.[CH3:7][C:8]1[CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:13])[O:11][CH:12]=1.[C:20]1([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1>[Br-:1].[CH3:7][C:8]1[CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:13])[O:11][C:12]=1[P+:26]([C:27]1[CH2:32][CH:31]=[CH:30][CH2:29][CH:28]=1)([C:33]1[CH2:34][CH:35]=[CH:36][CH2:37][CH:38]=1)[C:20]1[CH2:25][CH:24]=[CH:23][CH2:22][CH:21]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 67923942HCID 67923942, compound

Product 1

HCID 67923954HCID 67923954, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-Bromo-2,5-dihydrofuran-4-methyl-2-oxo-3-phenylfuran (3.46 g) and triphenylphosphine (4.14 g) in benzene (50 mls), were heated under reflux overnight. The colourless salt was filtered off, washed with benzene, then ether (2 portions), and dried to give the title compound as a white solid, (6.13 g, 85%), m.p. 214°-217° C. (decomp), acetonitrile/ethyl acetate. (Found: C, 67.21; H, 4.61; Br, 15.65%. C29H24BrO2P requires C, 67.58; H, 4.69; Br, 15.51%); νmax (CH2Cl2) 1775(s)cm-1 ; δH (CDCl3) 2.14 (3H,d,J4Hz), 7.1-8.5 (20H,m) and 9.75 (1H,d,J7Hz); [mass spectrum: +ve ion (thioglycerol) MH+, 435].

Workup

  1. temperatureunder reflux overnight
  2. filtrationThe colourless salt was filtered off
  3. washwashed with benzene
  4. dry with materialether (2 portions), and dried

Sources & evidence

ORD record
ord-71eadb77ff274d28907964278c56866a
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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