Ethyl Acetate → HCID 59615955, compound

To a cooled (0° C.) solution of 6-[3,5-Bis-(tert-butyl-dimethyl-silyloxymethyl)-phenyl]-hex-5-ynoic acid methyl ester (140 mg) in anhydrous tetrahydrofurane (0.3 mL) was slightly added a solution of tetrabutylammonium fluoride 1 M in THF (716 μL). After 75 min at rt, ethyl acetate (20 mL) was added and the organic phase was washed three times with water (5 mL) and once with a saturated aqueous solution of sodium chloride (5 mL), dried over sodium sulfate and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioFlash 15 g column, Si60 15-40 μm), using gradient elution with a mixture of heptane (A)/ethyl acetate (B), (gradient: 50% A: 50% B down to 10% A: 90% B) to give 6-(3,5-Bis-hydroxymethyl-phenyl)-hex-5-ynoic acid methyl ester (64.3 mg) as a pale yellow oil. LC/MS (Method A3): ES: m/z 263 (M+H)+; RT=0.62 min

1. washthe organic phase was washed three times with water (5 mL)
2. dry with materialonce with a saturated aqueous solution of sodium chloride (5 mL), dried over sodium sulfate
3. concentrationconcentrated in vacuo to a residue
4. customThe residue was purified by silica gel chromatography (Merck SuperVarioFlash 15 g column, Si60 15-40 μm)
5. washelution
6. additionwith a mixture of heptane (A)/ethyl acetate (B), (gradient: 50% A: 50% B down to 10% A: 90% B)

ORD record

ord-15a90120046f4831862f992be428bf9a

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404678B2