Water → HCID 86650297, compound

Temperature

50 °C

Thioacetic acid S-[2-(4-methanesulfonyloxy-phenyl)-ethyl]ester (250 mg, 0.91 mmol) was dissolved in anhydrous THF (2.5 mL) and LiAlH4 (38 mg, 1.0 mmol) was added in portions. After completed addition the mixture was warmed up to 50° C. and stirred for 1.5 h. The mixture was cooled down to 0° C. and excess LiAlH4 was hydrolyzed by the addition of H2O (0.8 mL), 2N aq. NaOH (1.0 mL) and THF (10 mL). Afterwards the reaction mixture was refluxed for 30 min then the precipitated salts were filtered off and the remaining filtrated was diluted with EtOAc. After extraction with brine and drying over Na2SO4, the solvent was evaporated under reduced pressure to afford the crude product as an oil (232 mg, 94.9%). 1H NMR (400 MHz, CDCl3): δ 7.29-7.31 (d, 2H), 7.21-7.23 (d, 2H), 3.31 (s, 3H), 2.81-2.85 (m, 2H), 2.68-2.73 (m, 2H).

1. additionaddition the mixture
2. temperatureThe mixture was cooled down to 0° C.
3. temperatureAfterwards the reaction mixture was refluxed for 30 min
4. filtrationthe precipitated salts were filtered off
5. filtrationthe remaining filtrated
6. additionwas diluted with EtOAc
7. extractionAfter extraction with brine
8. dry with materialdrying over Na2SO4
9. customthe solvent was evaporated under reduced pressure

ORD record

ord-3c156851c8314863b00584dfdb2fb955

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181181B2