Tetrabutylammonium Fluoride → 4-Hydroxymethyl-5-methyl-furan-2-carbonitrile
Reaction equation
C([SiH2][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[C:8]1[CH:9]=[C:10]([C:14]#[N:15])[O:11][C:12]=1[CH3:13])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([C:14]#[N:15])[O:11][C:12]=1[CH3:13]Participants
Procedure
A solution of 4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile from (ii) (3.75 g) in tetrahydrofuran (100 ml) was cooled to 0° C. under an argon atmosphere, and was treated with a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (22 ml). The mixture was allowed to warm to room temperature and stirred for 16 hours. The volatiles were removed and the residue was partitioned between ethyl acetate and water. The organic phase was separated and the aqueous phase was extracted with more ethyl acetate. The combined ethyl acetate extracts were washed with 1M aqueous hydrochloric acid and brine, and dried. The solvent was evaporated and the crude orange oil was purified by flash chromatography (silica, gradient elution with 0% to 40% ethyl acetate in cyclohexane) to afford compound 147 as a pale yellow oil (1.3 g).
Workup
- customThe volatiles were removed
- customthe residue was partitioned between ethyl acetate and water
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with more ethyl acetate
- washThe combined ethyl acetate extracts were washed with 1M aqueous hydrochloric acid and brine
- customdried
- customThe solvent was evaporated
- customthe crude orange oil was purified by flash chromatography (silica, gradient elution with 0% to 40% ethyl acetate in cyclohexane)
Sources & evidence
- ORD record
- ord-c328ae174be445669106f3786cb42798
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528157B2
Reaction notes
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