Triethyl phosphite → Diethyl [(2-ethyl-5-methyl-1,3-thiazol-4-yl)methyl]phosphonate

HRID 2221704Notes

Reaction equation

HRID 2221704 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH2:9][CH3:10])[S:6][C:7]=1[CH3:8].[P:11]([O:18]CC)([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>>[CH2:9]([C:5]1[S:6][C:7]([CH3:8])=[C:3]([CH2:2][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[N:4]=1)[CH3:10]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 230764064-Chloromethyl-2-ethyl-5-methyl-1,3-thiazole

Product 1

HCID 86605755Diethyl [(2-ethyl-5-methyl-1,3-thiazol-4-yl)methyl]phosphonateYield 97%

Conditions

Temperature
160 °C

Procedure

A mixture of 4-chloromethyl-2-ethyl-5-methyl-1,3-thiazole (3.2 g) and triethyl phosphite (6.7 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 (1:2-1:1, v/v) to give diethyl [(2-ethyl-5-methyl-1,3-thiazol-4-yl)methyl]phosphonate as a colorless oil (4.9 g, yield 97%).

Workup

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

Sources & evidence

ORD record
ord-1265314925eb4185a428288afc803302
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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