2-Thiophenecarboxaldehyde → HCID 59751486, compound

HRID 748650Notes

Reaction equation

[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=[O:5])=[O:4].[Li]CCCC.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH:30]=[O:31]>C1COCC1>[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[C:9]([CH:30]([OH:31])[C:26]2[S:25][CH:29]=[CH:28][CH:27]=2)[N:8]=[C:7]1[Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])(=[O:4])=[O:5]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of N,N-dimethyl imidazole-1-sulfonamide (commercially available from Aldrich) (1.5 g, 8.57 mmol) in THF (35 mL) at −78° C. was treated with nBuLi (5.4 mL of a 1.6 M soln) for 1 h. Solid TBSCl: tert-butyldimethylsilyl chloride (1.29 g, 8.6 mmol) in THF (5 mL) was added at rt for 16 h. The mixture was cooled to −20° C. and treated with nBuLi (5.9 mL of a 1.6 M soln) for 1 h. Thiophene-2-carbaldehyde (commercially available from Aldrich) (0.96 mL, 10.3 mmol) in THF (10 mL) is added and the mixture was stirred for 3 h at rt. The mixture was washed with brine and dried over Na2SO4. The solvent was removed under vacuum and the residue was purified by chromatography on silical gel with 30% EtOAc: hexane to give 2-(tert-butyl-dimethyl-silanyl)-4-(hydroxy-thiophen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (Intermediate-E1) 2.5 g.

Workup

washThe mixture was washed with brine
dry with materialdried over Na2SO4
customThe solvent was removed under vacuum
customthe residue was purified by chromatography on silical gel with 30% EtOAc

Sources & evidence

ORD record: ord-68cfe2b8a6234fb894e494fdaf58161c
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399868B2

Reaction notes

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