Dimethylformamide → HCID 20077568, compound

HRID 1655077Notes

Reaction equation

[Si:1]([C:8]1[S:9][CH:10]=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.CN(C)[CH:20]=[O:21].[Cl-].[NH4+]>CCOCC>[Si:1]([C:8]1[S:9][C:10]([CH:20]=[O:21])=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of compound Q (40 g) in ether (100 ml) was added dropwise to a solution of n-butyllithium (1.6M solution in hexane, 138 ml) in ether (300 ml) at -70° C. under an atmosphere of argon. The mixture was stirred for 1 hour at this temperature and then N,N-dimethylformamide (30 ml) was added dropwise. The mixture was stirred for 30 minutes at -70° C., then warmed to -40° C. Excess saturated aqueous ammonium chloride solution was added and the mixture allowed to warm to ambient temperature. The layers were separated and the aqueous phase extracted three times with ether. The organic phases were combined, dried (MgSO4), and concentrated. The residue was purified by column chromatography, eluting with 25% ethyl acetate/hexane (v/v), to give 2-tert-butyldimethylsilylthiazole-5-carboxaldehyde (R) (31 g, 69% yield) as an oil; NMR: 0.32(6H,s), 0.89(9H,s), 8.55(1H,s), 10.0(1H,s).

Workup

stirringThe mixture was stirred for 30 minutes at -70° C.
temperatureto warm to ambient temperature
customThe layers were separated
extractionthe aqueous phase extracted three times with ether
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified by column chromatography
washeluting with 25% ethyl acetate/hexane (v/v)

Sources & evidence

ORD record: ord-9bc15ac4859a44779678ad779b214c40
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05410064

Reaction notes

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