Tetrahydrofuran → 1-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde

HRID 2269172Notes

Reaction equation

[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=[O:5])=[O:4].C1C[O:22][CH2:21]C1.C([Li])(CC)C.CCCCCC>O.CN(C)C=O>[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[C:10]([CH:21]=[O:22])=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])(=[O:4])=[O:5]

Participants

Conditions

Temperature: -20 °C

Procedure

1-Dimethylsulfamoyl-2-t-butyldimethylsilyl imidazole (3) (5.0 g, 17.3 mmol) was added to 100 mL of THF. The solution was cooled to −20° C. A solution of secondary butyl lithium (s-BuLi) in hexane (1.3M, 14.6 mL, 19 mmol) was added dropwise to the reaction flask. Upon completion the reaction was stirred for 1 h at −20° C. 8 mL of dimethylformamide (DMF) was added to the reaction and then stirred at rt for 3.5 h. The reaction was diluted with water and the organic layer separated. The organic phase was washed with brine and then dried over sodium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure. Column chromatography (20% ethyl acetate/hexane) afforded a light yellow oil. Upon cooling the product solidifies to give yellow crystals of 1-dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde (4).

Workup

stirringstirred at rt for 3.5 h
customthe organic layer separated
washThe organic phase was washed with brine
dry with materialdried over sodium sulfate
filtrationThe mixture was filtered
concentrationthe filtrate concentrated under reduced pressure
customColumn chromatography (20% ethyl acetate/hexane) afforded a light yellow oil
temperatureUpon cooling the product

Sources & evidence

ORD record: ord-0552574515fd49fb88e740eec5de01bb
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329369B1

Reaction notes

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