Dichloromethane → t-Butyl (triphenylphosphoranylidene)propionate

HRID 330175Notes

Reaction equation

HRID 330175 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:21]([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(N(CC)CC)C.C(Cl)Cl>C(OCC)(=O)C>[C:14]1([P:7](=[C:21]([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 545327tert-Butyl 2-bromopropanoate

Product 1

HCID 10916149t-Butyl (triphenylphosphoranylidene)propionateYield 80.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The t-butyl (triphenylphosphoranylidene)propionate was prepared as follows: Triphenylphosphine (33 g), t-butyl 2-bromopropionate (22 g) and triethylamine (12.7 g) were dissolved in ethyl acetate (150 ml), and stirred and heated under reflux for 48 hr, under an atmosphere of nitrogen. Methylene chloride (300 ml) was added to the cooled solution; the mixture was thoroughly washed with sodium hydroxide solution (10% w/w, 300 ml), water (200 ml) and brine; and dried (MgSO4). The solvent was evaporated and the residual oil triturated with hexane (2×200 ml) to give t-butyl (triphenylphosphoranylidene)propionate (33 g, 67%) as a yellow powder; mp 144°-151°; partial NMR (250 MHz, CDCl3): 1.0(br signal, 9H, t-butyl), 1.55(d, J=14.4 Hz, 3H, CH3), 7.3-7.9(complex m, 15H, ArH).

Workup

  1. customThe t-butyl (triphenylphosphoranylidene)propionate was prepared
  2. temperatureheated
  3. temperatureunder reflux for 48 hr, under an atmosphere of nitrogen
  4. washthe mixture was thoroughly washed with sodium hydroxide solution (10% w/w, 300 ml), water (200 ml) and brine
  5. dry with materialand dried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residual oil triturated with hexane (2×200 ml)

Sources & evidence

ORD record
ord-1496e1714140416aa62ae838efcb74cc
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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