Triethyl phosphite → Diethyl [(2-phenyl-1,3-oxazol-5-yl)methyl]phosphonate

HRID 2248976Notes

Reaction equation

HRID 2248976 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][CH:4]=1.[CH2:14]([O:16][P:17]([O:21]CC)[O:18][CH2:19][CH3:20])[CH3:15]>>[CH2:14]([O:16][P:17]([CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][CH:4]=1)([O:18][CH2:19][CH3:20])=[O:21])[CH3:15]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 150263445-(Chloromethyl)-2-phenyl-1,3-oxazole

Product 1

HCID 53729758Diethyl [(2-phenyl-1,3-oxazol-5-yl)methyl]phosphonateYield 60%

Procedure

5-Chloromethyl-2-phenyl oxazole (870 mgs, 4.50 mmol) and triethylphosphite (1.17 ml, 6.75 mmol) were heated at reflux for 3 h, cooled, the excess triethylphosphite removed under reduced pressure and the residue column chromatographed (0 to 5% MeOH/CH2Cl2, 10 g silica) to give the title compound (794 mgs, 2.69 mmol, 60%); δH (CDCl3) 1.30(6H,t,J 7 Hz,OCH2CH3), 3.30(2H,d,JP-H 22 Hz,CH2 -P) 4.10(4H,m,OCH2CH3), 7.00(1H,d,JP-H 3 Hz,CH-4), 7.40(3H,m,Ph), 8.00(2H,m,Ph).

Workup

  1. temperatureat reflux for 3 h
  2. temperaturecooled
  3. customthe excess triethylphosphite removed under reduced pressure
  4. customthe residue column chromatographed (0 to 5% MeOH/CH2Cl2, 10 g silica)

Sources & evidence

ORD record
ord-cca5fccef0154aaea80e6fc6a87f62f5
Source dataset
uspto-grants-1991_08
Patent number
US05041567

Reaction notes

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