Chlorotrimethylsilane → HCID 10313521, compound

HRID 727247Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.C([Li])CCC.C[Si](Cl)(C)C.[O:17]1[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18]1.C(=O)([O-])O.[Na+]>C(OCC)C>[O:17]1[CH:21]=[CH:20][C:19]([CH:22]([C:6]2[S:5][CH:4]=[N:3][C:2]=2[CH3:1])[OH:23])=[CH:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Methylthiazole (3g) in dry diethyl ether was added dropwise to a stirred solution of n-butyllithium (1.6M in hexanes, 21ml) in diethyl ether (20ml) at -78° C. under an atmosphere of dry nitrogen. After 30 minutes, trimethylsilylchloride (3.9ml) was added and the mixture was then allowed to warm to 0° C. The mixture was then cooled to -78° C. and further n-butyllithium (21ml) was added. The mixture was warmed to 0° C. After 30 minutes the mixture was again cooled to -78° C. and 3-furaldehyde (5g) in diethyl ether (10ml) was added. The mixture was allowed to warm to room temperature and after 30 minutes saturated aqueous sodium hydrogen carbonate was added. The reaction mixture was extracted with diethyl ether in the usual manner to give the crude product which was then purified by flash chromatography on silica gel to give the title compound. M.p. 44°-46° C.

Workup

temperatureThe mixture was then cooled to -78° C.
temperatureThe mixture was warmed to 0° C
temperatureAfter 30 minutes the mixture was again cooled to -78° C.
additionwas added
extractionThe reaction mixture was extracted with diethyl ether in the usual manner
customto give the crude product which
customwas then purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-29809dfebc654c1fa0cbb8c7df62b65d
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712299

Reaction notes

Loading…