Carbon Tetrachloride → 3-(Chloromethyl)-5-phenyl-1,2-oxazole

HRID 1194063Notes

Reaction equation

HRID 1194063 reaction equation
O[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:34]>>[Cl:34][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 1481082(5-Phenyl-1,2-oxazol-3-yl)methanol

Product 1

HCID 14847693-(Chloromethyl)-5-phenyl-1,2-oxazoleYield 58%

Procedure

3-Hydroxymethyl-5-phenylisoxazole (2.10 g, 12 mmol) was refluxed with triphenylphosphine (3.14 g, 12 mmol) in carbon tetrachloride (40 ml) overnight. After cooling the solvent was removed under reduced pressure and the residue taken up in ether, the solution filtered and concentrated to give an oil. This material was filtered through a plug of silicagel (5 g, ether-hexane 1:1) to remove triphenylphosphine oxide then crystallised to give the title compound (1.33 g, 6.9 mmol, 58%); m.p. 48°-9° C.; νmax (CHCl3) 3000, 1610, 1590, 1570, 1450, 1265, 945, 690 cm-1 ; δH (CDCl3) 4.55 (2H, s, CH2Cl), 6.55 (1H, s, CH-het) 7.2-8.0 (5H, m, Ph).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed under reduced pressure
  3. filtrationthe solution filtered
  4. concentrationconcentrated
  5. customto give an oil
  6. filtrationThis material was filtered through a plug of silicagel (5 g, ether-hexane 1:1)
  7. customto remove triphenylphosphine oxide
  8. customthen crystallised

Sources & evidence

ORD record
ord-355ee225869b45988cca34a603e7ba62
Source dataset
uspto-grants-1989_03
Patent number
US04812470

Reaction notes

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