Chlorotrimethylsilane → 1-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

HRID 975058

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.C([Li])CCC.C[Si](Cl)(C)C.[C:17]([C:20]1[CH:24]=[C:23]([CH3:25])[O:22][C:21]=1[CH3:26])(=[O:19])[CH3:18].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:26][C:21]1[O:22][C:23]([CH3:25])=[CH:24][C:20]=1[C:17]([C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1])([OH:19])[CH3:18]

Participants

Conditions

Temperature: -70 °C

Procedure

4-Methylthiazole (6.51 g) in dry tetrahydrofuran (50 ml) was stirred under an atmosphere of dry nitrogen and cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes trimethylsilylchloride (7.14 g) was added and the mixture was allowed to warm to room temperature. After 30 minutes the mixture was again cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes 3-acetyl-2,5-dimethylfuran (10 g) was added dropwise. The mixture was stirred at -70° C. for 1 hour and was then allowed to warm to room temperature. After 30 minutes, aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The combined extracts were washed, dried and evaporated to give the title compound which was recrystallised from diethylether. M.p. 100.5°-101.5° C.

Workup

temperatureto warm to room temperature
temperatureAfter 30 minutes the mixture was again cooled to -70° C.
temperatureto warm to room temperature
waitAfter 30 minutes
extractionthe mixture was extracted with diethylether
washThe combined extracts were washed
customdried
customevaporated

Sources & evidence

ORD record: ord-8a40174422a440fbb1fa16755cf0c042
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05607956

Linked notes

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