Triethyl phosphite → HCID 86605753, compound

HRID 2221686Notes

Reaction equation

HRID 2221686 reaction equation
[C:1]([O:9][CH2:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16]Cl)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:18]([O:25]CC)([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>C(OCC)(=O)C>[C:1]([O:9][CH2:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][P:18]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:25])[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 23371811HCID 23371811, compound

Product 1

HCID 86605753HCID 86605753, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (4-chloromethyl-1,3-thiazol-2-yl)methyl benzoate (6.4 g), triethyl phosphite (8.7 g) was stirred at 150° C. for 17 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, v/v)-ethyl acetate to give {4-[(diethoxyphosphoryl)methyl]-1,3-thiazol-2-yl}methyl benzoate as a yellow oil (8.0 g, yield 91%).

Workup

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

Sources & evidence

ORD record
ord-ca868c301a2348ffb0ca72c8f3f16ac3
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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