Methanol → HCID 71519611, compound

Temperature

0 °C

A 1-L round-bottom flask was charged with a solution of 6 (14.9 g, 73.6 mmol) in MeOH (240 mL) and cooled to 0° C. A solution of NaIO4 (16.5 g, 77.3 mmol) in water (180 mL) was added via addition funnel over ˜15 min. The ice bath was removed and the slurry was warmed to rt. MeOH (2×50 mL, added 20 min apart) was added, and the mixture was stirred for 12 h at rt. The mixture was filtered through a fritted funnel, and the white precipitate was washed with MeOH. The combined filtrate and washings were concentrated in vacuo, and the concentrate was coevaporated with toluene (200 mL). CH2Cl2 (400 mL) was added to the residue, followed by MgSO4. The mixture was filtered, and the filtrate was concentrated in vacuo to afford crude 3 (15.82 g) as a yellow solid. To the flask containing the crude solid was added toluene (200 mL), and the slurry was heated to 60° C. to affect complete dissolution. Decolorizing carbon was added, and the mixture was filtered by gravity into a 1-L Erlenmeyer flask. To the colorless solution was slowly added distilled hexanes (˜100 mL total) until cloudiness/precipitation occurred. The mixture was allowed to stand at rt overnight. Upon filtration and drying under high vacuum, 3 (10.49 g) was collected as a white solid. Material recovered from the mother liquor was recrystallized to afford an additional 2.68 g of 3 as white solid for a total yield of 82%. Reported analytical data refer to that of the first crop: Mp 92.8-94.1° C.; IR (ATR) 2939, 2863, 1451, 1381, 1227, 1026, 971 cm−1; H NMR (400 MHz, CDCl3) δ 4.80 (d, J=6.0 Hz, 2H), 4.61 (d, J=5.6 Hz, 2H), 4.50 (d, J=5.4 Hz, 2H), 4.45 (d, J=6.0 Hz, 2H), 3.38 (d, J=12.9 Hz, 2H), 2.75 (d, J=12.9 Hz, 2H), 1.61 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 82.4, 82.0, 61.9, 38.4, 23.4; HRMS (ES) m/z calc for C10H18O3NaS (M+Na) 241.0874. found 241.0885.

1. customThe ice bath was removed
2. temperaturethe slurry was warmed to rt
3. additionMeOH (2×50 mL, added 20 min apart)
4. additionwas added
5. filtrationThe mixture was filtered through a fritted funnel
6. washthe white precipitate was washed with MeOH
7. concentrationThe combined filtrate and washings were concentrated in vacuo
8. additionCH2Cl2 (400 mL) was added to the residue
9. filtrationThe mixture was filtered
10. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-f0de823c3d644bc3b2a770d52146ac69

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200035B2