Tetrabutylammonium Fluoride → HCID 178525696, compound

Tetrabutylammonium fluoride (0.12 ml) was added to a stirred solution of 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanecarboxylic acid (22 mg) in tetrahydrofuran (1 ml) at room temperature under argon. After 24 hr, the reaction mixture was partitioned between ethyl acetate (30 ml) and water (30 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 ml). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 7:1 v/v, <1% acetic acid) to give the title compound as an orange solid (10 mg, 89%). δH(CD3OD) 1.40-1.65 (4H, m), 1.88-1.95 (2H, m), 2.06-2.14 (2H, m), 2.35 (1H, tt), 2.82 (1H, it), 6.25-6.30 (2H, m), 6.90 (1H, d); m/z (ES−) 235 (M−H)−.

1. customthe reaction mixture was partitioned between ethyl acetate (30 ml) and water (30 ml)
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with ethyl acetate (2×30 ml)
4. dry with materialThe combined organic extracts were dried over magnesium sulfate
5. customevaporated in vacuo
6. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 7:1 v/v, <1% acetic acid)

ORD record

ord-6e048efc956f4577a48ea074f3fccaf5

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06828460B2