Triethyl phosphite → HCID 86605750, compound

HRID 2221685Notes

Reaction equation

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

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 164949712-Tert-butyl-4-(chloromethyl)-1,3-thiazole

Product 1

HCID 86605750HCID 86605750, compoundYield 90.2%

Conditions

Temperature: 160 °C

Procedure

A mixture of 2-tert-butyl-4-chloromethyl-1,3-thiazole (8.66 g) and triethyl phosphite (15.7 g) was stirred at 160° C. for 20 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 to 1:0, v/v) to give diethyl [(2-tert-butyl-1,3-thiazol-4-yl)methyl]phosphonate as a colorless oil (12.0 g, yield 90%).

Workup

customExcess triethyl phosphite was evaporated under reduced pressure
washeluted with ethyl acetate-hexane (1:2 to 1:0

Sources & evidence

ORD record: ord-cf9a6e6041964a238563aef65ea1234b
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

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