Triphenylphosphine → HCID 21466821, compound

HRID 1939120Notes

Reaction equation

HRID 1939120 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][C:5]([CH3:9])([CH2:7]O)[N:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:29]N1C(=O)CCC1=O>ClCCl>[CH3:1][C:2]1[O:3][CH2:4][C:5]([CH3:9])([CH2:7][Br:29])[N:6]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 980734-Oxazolemethanol, 4,5-dihydro-2,4-dimethyl-

Product 1

HCID 21466821HCID 21466821, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 40.1 g (310 mmol) of 2,4-dimethyl-4-hydroxymethyl-2-oxazoline (J. Nys and J. Libeer, Bull. Soco Chim. Belg., 65, 377 (1956)) and 85.5 g (326 mmol) of triphenylphosphine in 400 ml of dichloromethane is mixed at 0° C. in portions with 58.0 g (326 mmol) of N-bromosuccinimide and then stirred overnight at room temperature. The solution is concentrated by evaporation and the residue is pulverized with tert-butyl methyl ether. A precipitate develops, which is separated and washed with tert-butyl methyl ether. The combined filtrates are subjected to a fractionated distillation at normal pressure, and first the solvent is drawn off and then the title compound is distilled at an oil bath temperature of 200° C.

Workup

  1. concentrationThe solution is concentrated by evaporation
  2. customwhich is separated
  3. washwashed with tert-butyl methyl ether
  4. distillationThe combined filtrates are subjected to a fractionated distillation at normal pressure
  5. distillationthe title compound is distilled at an oil bath temperature of 200° C.

Sources & evidence

ORD record
ord-8bd1310b68e74a268dc196b72ce1e5ab
Source dataset
uspto-grants-1997_12
Patent number
US05695737

Reaction notes

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