Pentadecalactone → Methyl 15-Hydroxypentadecanoate

Sodium methoxide was generated by the addition of sodium metal (2.4 g, 104.3 mmol, 5.0 eq) to methanol (130 mL) at 0° C. with stirring. The mixture was warmed to room temperature and stirred until all of the sodium was consumed. ω-Pentadecalactone (5.0 g, 20.8 mmol, 1.0 eq) was added in a single portion, and the solution was stirred at 80° C. for 3 hours. The reaction was quenched with hydrochloric acid (1 M, 175 mL) and diluted with water (175 mL). The aqueous layer was extracted with ether (3×100 mL), and the combined organic layers were washed with water (150 mL), brine (150 mL), and dried over magnesium sulphate. The product was purified by silica gel chromatography (2:1 hexane:ethyl acetate), yielding methyl 15-hydroxypentadecanoate (4.24 g, 85%) as a colourless solid.

1. customwas consumed
2. stirringthe solution was stirred at 80° C. for 3 hours
3. customThe reaction was quenched with hydrochloric acid (1 M, 175 mL)
4. additiondiluted with water (175 mL)
5. extractionThe aqueous layer was extracted with ether (3×100 mL)
6. washthe combined organic layers were washed with water (150 mL), brine (150 mL)
7. dry with materialdried over magnesium sulphate
8. customThe product was purified by silica gel chromatography (2:1 hexane:ethyl acetate)

ORD record

ord-5cc4d2cfa6fb4fc497d9912b7d6faa3c

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09287114B2