HCID 14264940, compound → HCID 69058415, compound

HRID 1432807Notes

Reaction equation

HRID 1432807 reaction equation
Cl[C:2]1([CH3:12])[CH:11]2[CH:3]1[CH2:4][CH2:5][C:6]12[O:10][CH2:9][CH2:8][O:7]1.CC([O-])(C)C.[K+]>CS(C)=O>[CH2:12]=[C:2]1[CH:11]2[CH:3]1[CH2:4][CH2:5][C:6]12[O:7][CH2:8][CH2:9][O:10]1

Participants

4

Reactant 2

HCID 14264940HCID 14264940, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69058415HCID 69058415, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (±)-6-chloro-6-methyl-spiro[bicyclo[3.1.0]hexane-2,2′-[1,3]dioxolane] (2.50 g, 13.25 mmol) in DMSO (40 mL) was added a solution of KOtBu (15.9 mL of 1.0M in THF). The solution heated at 60 ° C. overnight. After cooling down the reaction mixture to rt, the product was extracted into n-Hexane. Solvent was removed under reduced pressure. SiO2 column chromatography (14-25% EtOAc/n-hexane) gave the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 5.55 (s, 1H), 5.42 (t, 1H, J=1.0 Hz), 4.08-3.91 (m, 4H), 2.07-1.97 (m, 2H), 1.90-1.84 (m, 2H), 1.65-1.54 (m, 2H).

Workup

  1. temperatureAfter cooling down the reaction mixture to rt
  2. extractionthe product was extracted into n-Hexane
  3. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b092246971e049e79f4ee60c153234e9
Source dataset
uspto-grants-2009_11
Patent number
US07612106B2

Reaction notes

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