Triphenylphosphine → HCID 67923948, compound

HRID 973872Notes

Reaction equation

HRID 973872 reaction equation
[Br:1][CH:2]1[O:6][C:5](=[O:7])[C:4]([CH3:8])=[C:3]1[O:9][CH3:10].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1C=CC=CC=1>[Br-:1].[CH3:10][O:9][C:3]1[CH:4]([CH3:8])[C:5](=[O:7])[O:6][C:2]=1[P+:17]([C:18]1[CH2:23][CH:22]=[CH:21][CH2:20][CH:19]=1)([C:24]1[CH2:25][CH:26]=[CH:27][CH2:28][CH:29]=1)[C:11]1[CH2:16][CH:15]=[CH:14][CH2:13][CH:12]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 19988399HCID 19988399, compound

Product 1

HCID 67923948HCID 67923948, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-Bromo-2,5-dihydro-4-methoxy-3-methyl-2-oxofuran (6.44 g) was dissolved in dry benzene (100 mls). Triphenylphosphine was added and the solution stirred overnight at room temperature. The solution was decanted from the orange gum, which was then triturated with ether to give a colourless crystalline solid. The ether was decanted and the salt dried under vacuum. The decanted solution was concentrated to a gum. Trituration of this with ether resulted in a second crop of the phosphonium salt. The combined crops gave the title compound as a colourless solid, (14 41 g, 99%), νmax (CH2Cl2) 1775, 1665, 1435, 1390 and 1330cm-1 ; δH (CDCl3) 1.74 (3H, m), 3.95 (3H, s) and 7.5-8.1 (16H, m); [mass spectrum: +ve ion (3NOBA, Na+) M+ -Br, 389].

Workup

  1. customThe solution was decanted from the orange gum, which
  2. customwas then triturated with ether
  3. customto give a colourless crystalline solid
  4. customThe ether was decanted
  5. customthe salt dried under vacuum
  6. concentrationThe decanted solution was concentrated to a gum

Sources & evidence

ORD record
ord-4dc41db48a714890bac65186905ab619
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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