6-Oxabicyclo[3.1.0]hexane → HCID 60155352, compound

HRID 1506864Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([O:12]C)=[O:11].[CH:15]12[O:20][CH:16]1[CH2:17][CH2:18][CH2:19]2.[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][C@H:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[OH:20])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of compound (8) (3.50 g, 17.7 mmol) in dry DMF (35 mL), cyclopentene oxide (2.3 mL, 26.6 mmol) and sodium hydride (0.64 g, 26.6 mmol) were added and stirred at 70° C. for 14 hours. After completion of the reaction, the obtained mixture was cooled to room temperature and concentrated under reduced pressure. The residue was extracted with ethyl acetate (300 mL) followed by washing with water and drying (over sodium sulfate). The solvent was distilled off, and the residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (8:1) solution followed by conventional hydrolysis to give 2.60 g (52%) of compound (13) of interest as yellow oil.

Workup

customAfter completion of the reaction
temperaturethe obtained mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
extractionThe residue was extracted with ethyl acetate (300 mL)
washby washing with water
dry with materialdrying (over sodium sulfate)
distillationThe solvent was distilled off
washthe residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (8:1) solution
customfollowed by conventional hydrolysis

Sources & evidence

ORD record: ord-9b9ff7054945423ea0eae3576541c028
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221786B2

Reaction notes

Loading…