Water → HCID 66683082, compound

HRID 909425Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][N:10]=1.[H-].[Na+].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14].O>CN(C)C=O.C(OCC)C>[CH:13]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][N:10]=1)([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

2-(1H-Pyrrol-2-yl)-1,3-thiazole (1.42 g, 9.45 mmol) known in the literature {Eur. J. Org. Chem. (European Journal of Organic Chemistry) vol. 2000, no. 13, 2449-2458 (2000)} was dissolved in N,N-dimethylformamide (100 mL), and cooled to 0° C. Sodium hydride (60% oil, 570 mg, 14.3 mmol) and triisopropylsilyl chloride (4.0 mL, 18.7 mmol) were added, and stirring was carried out at room temperature for 30 minutes under nitrogen atmosphere. Water (100 mL) and diethyl ether (100 mL) were added, and the solution was separated. The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: hexane) to afford the desired compound (2.33 g, yield 80%) as a pale yellow oil.

Workup

customthe solution was separated
washThe organic layer was washed with saturated brine
dry with materialsubsequently dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified
washsilica gel column chromatography (elution solvent: hexane)

Sources & evidence

ORD record: ord-82960b1ff4004b6496aad7a973a9e97e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017610B2

Reaction notes

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