Chlorotrimethylsilane → 2-Trimethylsilylthiazole

HRID 1660735Notes

Reaction equation

C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.Cl[Si:12]([CH3:15])([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+]>C(OCC)C>[CH3:13][Si:12]([CH3:15])([CH3:14])[C:7]1[S:6][CH:10]=[CH:9][N:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Mix n-butyl lithium (20.4 mL, 51.0 mmol, 2.5 M in hexane) with diethyl ether (50 mL) in a three-necked flask, equipped with a dropping funnel and thermometer. Cool to −78° C. and add dropwise a solution of thiazole (4.25 g, 50.0 mmol) in diethyl ether (50 mL). After the addition is complete, stir the reaction mixture at −78° C. for 30 min, followed by addition of chlorotrimethylsilane (5.4 g, 50.0 mmol). Stir at −78° C. for an hour and then warm to room temperature. Quench the reaction by adding saturated sodium bicarbonate. Extract the aqueous layer with diethyl ether. Wash the combined organic portions with brine and dry over sodium sulfate. Filter and concentrate under reduced pressure to give a residue. Purify by distillation to give 8.33 g (52-56° C./15 mm Hg) of title compound. 1H NMR (400 MHz, CDCl3) 8.13 (d, 1H, J=2.6 Hz), 7.54 (d, 1H, J=2.6 Hz), 0.43 (s, 9H).

Workup

customequipped with a dropping funnel
additionAfter the addition
stirringStir at −78° C. for an hour
temperaturewarm to room temperature
customQuench
customthe reaction
extractionExtract the aqueous layer with diethyl ether
washWash the combined organic portions with brine
dry with materialdry over sodium sulfate
filtrationFilter
concentrationconcentrate under reduced pressure
customto give a residue
distillationPurify by distillation

Sources & evidence

ORD record: ord-89c3313845eb4235a83b69930c6ef1a2
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030304B2

Reaction notes

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