Ethyl Acetate → Diethyl [(2-ethyl-1,3-oxazol-4-yl)methyl]phosphonate

HRID 2221674Notes

Reaction equation

HRID 2221674 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH2:8][CH3:9])[O:6][CH:7]=1.[P:10]([O:17]CC)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].C(OCC)(=O)C>C(OCC)(=O)C.C(O)C>[CH2:8]([C:5]1[O:6][CH:7]=[C:3]([CH2:2][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[N:4]=1)[CH3:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31215Triethyl phosphiteHCID 23076478HCID 23076478, compound

Product 1

HCID 85954647Diethyl [(2-ethyl-1,3-oxazol-4-yl)methyl]phosphonateYield 70%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-chloromethyl-2-ethyl-1,3-oxazole (3.26 g), triethyl phosphite (8.19 g) was stirred at 160° C. for 16 hrs. Excess triethyl phosphite was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:1, v/v), ethyl acetate, then ethyl acetate-ethanol (10:1, v/v) to give diethyl [(2-ethyl-1,3-oxazol-4-yl)methyl]phosphonate as a colorless oil (3.86 g, yield 70%).

Workup

  1. customExcess triethyl phosphite was evaporated under reduced pressure
  2. washeluted with ethyl acetate-hexane (1:1

Sources & evidence

ORD record
ord-1846be0ea06e4fa1804b692be89c3123
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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