Potassium Hydroxide → HCID 71696925, compound

Temperature

0 °C

To the solution of allene (48. mg, 0.230 mmol) in 1:1 solution of t-BuOH and pH 7.4 buffer (3.0 ml) at rt was added NMO (60. mg, 0.460 mmol) and 4 wt % OsO4 in water (0.300 ml, 0.046 mmol). NBS (77. mg, 0.460 mmol) was dissolved in 1:1:1 solution of t-BuOH, water and acetone (3.00 ml) and added to the reaction mixture via syringe pump over 5 h at rt. After the complete consumption of allene as judged by TLC (5 h), the reaction was quenched by a saturated solution of sodium sulfite (3.00 ml). The reaction was diluted by water and the organic layer was extracted in EtOAc (3×10.0 ml), dried over anhydrous Na2SO4, filtered, concentrated and purified by flash column chromatography (4% EtOAc/Hexane) to obtain 4-bromo-6-butyl-6-hydroxy-2-methyldecan-5-one (63. mg, 85% yield) as colorless oil. The 4-bromo-6-butyl-6-hydroxy-2-methyldecan-5-one (63. mg, 0.196 mmol) was dissolved in DMSO (3.92 ml) and cooled to 0° C. To the reaction at 0° C. was added KOH (0.180 ml, 0.216 mmol) dropwise. Upon the completion of reaction as judged by TLC (10 min), the reaction was diluted with water and the organic layer was extracted in EtOAc (3×5.00 ml), dried over anhydrous Na2SO4, filtered, concentrated and purified by flash column chromatography (2% EtOAc/Hexane) to obtain 2,2-dibutyl-4-isobutyloxetan-3-one (45. mg, 95% yield) as colorless oil.

1. customTo the reaction at 0° C.
2. customUpon the completion of reaction
3. customas judged by TLC (10 min)
4. extractionthe organic layer was extracted in EtOAc (3×5.00 ml)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. custompurified by flash column chromatography (2% EtOAc/Hexane)

ORD record

ord-3fec359203d94dd9b26b8c6f86739fa1

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796474B1