Acetonitrile → HCID 86733263, compound

HRID 1606222Notes

Reaction equation

HRID 1606222 reaction equation
[Br:1][CH2:2][C@H:3]([CH3:9])[CH2:4][CH2:5][C:6]([OH:8])=[O:7].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(#N)C>C(OCC)C>[Br-:1].[C:6]([CH2:5][CH2:4][CH:3]([CH3:9])[CH2:2][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 86733265HCID 86733265, compound

Product 1

HCID 86733263HCID 86733263, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of 61.3 g. of (R)-5-bromo-4-methylpentanoic acid [J. S. Dalby et al., J. Chem. Soc., 1962, 4387], 92.0 g. of triphenylphosphine, and 160 ml. of acetonitrile is refluxed for 96 hours. The solution is cooled until crystallization begins and then diluted with 750 ml. of diethyl ether to complete the precipitation. The salt is obtained by filtration and is dried in vacuo at 75°C., m.p. 151°-164°C.

Workup

  1. temperatureThe solution is cooled until crystallization
  2. additiondiluted with 750 ml
  3. customthe precipitation
  4. customThe salt is obtained by filtration
  5. customis dried in vacuo at 75°C.

Sources & evidence

ORD record
ord-780b0aefa2854da889640335d04501a9
Source dataset
uspto-grants-1976_04
Patent number
US03952033

Reaction notes

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