14-(Tert-butoxy)-14-oxotetradecanoic acid → Tert-butyl 14-hydroxytetradecanoate

1 M Solution of borane-tetrahydrofuran complex in tetrahydrofuran (52 mL, 52.0 mmol) was added dropwise to a solution of tetradecanedioic acid mono-tert-butyl ester (10.0 g, 31.9 mmol) in dry tetrahydrofuran (75 mL) at 0 C under argon. The resulting solution was stirred at 0 C for 2 hrs, then the cooling bath was removed and the mixture stirred at room temperature overnight. Saturated aqueous solution of sodium hydrogencarbonate (150 mL) was added and the resulting mixture was extracted with dichloromethane (3×100 mL). Combined organic extracts were extracted with 5% aqueous solution of sodium carbonate (1×150 mL) and 10% aqueous solution citric acid (1×100 mL). Combined organic extracts were dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was subjected to column chromatography (Silicagel 60A, 0.060-0.200 mm; eluent: dichloromethane/methanol 100:0-99:1) to give 14-hydroxy-tetradecanoic acid tert-butyl ester as yellowish oil.

1. customthe cooling bath was removed
2. stirringthe mixture stirred at room temperature overnight
3. additionSaturated aqueous solution of sodium hydrogencarbonate (150 mL) was added
4. extractionthe resulting mixture was extracted with dichloromethane (3×100 mL)
5. extractionCombined organic extracts were extracted with 5% aqueous solution of sodium carbonate (1×150 mL) and 10% aqueous solution citric acid (1×100 mL)
6. dry with materialCombined organic extracts were dried over anhydrous magnesium sulfate
7. customevaporated to dryness

ORD record

ord-5fa6d73863f5466c9be105894efac3a3

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085637B2