tert-Butanol → HCID 57425849, compound

In a 10 mL flask with 3-benzyloxymethyl-1-cyclobutene (0.1 g, 0.57 mmol) inside, 0.72 mL tBuOMe, 1.54 mL tBuOH and 0.54 mL H2O were added to give two layers. Then NMO (50% wt sol. in H2O, 0.36 mL, 1.71 mmol) and OsO4 (0.07 mL, 0.06 mmol) were added drop by drop successively to give a light brown solution. This was left stirring at room temperature. After 3 hr, the solution was diluted with H2O and extracted with EtOAc three times. The organic layer was washed with brine once, dried over MgSO4 and concentrated. The crude product was purified by silica gel flash chromatography (Hexane:EtOAc=3:1 to Hexane: EtOAc=1:1) to give 27.4 mg (23%) the desired product. 1H NMR (CDCl3, 300 MHz): δ 1.70-1.92 (m, 2H), 2.46-2.75 (m, 1H), 3.02-3.2 (m, 1H), 3.2-3.34 (m, 1H), 3.4-3.6 (m, 2H), 3.90-4.10 (m, 1H), 4.2-4.4 (m, 1H), 4.4-4.6 (s, 2H), 7.21-7.50 (m, 5H). 13C NMR (CDCl3, 100 MHz): δ 28.08, 43.45, 68.32, 70.19, 71.41, 73.28, 127.83, 128.61, 138.56. IR (neat) νmax 3376, 2937, 2856, 1453, 1098, 738, 698.

1. customto give two layers
2. customto give a light brown solution
3. waitThis was left
4. extractionextracted with EtOAc three times
5. washThe organic layer was washed with brine once
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe crude product was purified by silica gel flash chromatography (Hexane:EtOAc=3:1 to Hexane: EtOAc=1:1)

ORD record

ord-3743d15fe34e4c22b5669c72e2efe6cc

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495006B2