Methanol → HCID 68773599, compound

HRID 1471377Notes

Reaction equation

HRID 1471377 reaction equation
CO.[CH3:3][C@@H:4]1[CH:11]=[CH:10][CH2:9][C:6]2([CH2:8][CH2:7]2)[C@@H:5]1[C:12](=[O:14])[CH3:13].[NH4+].[Cl-]>CCCCC>[CH3:3][C@@H:4]1[CH:11]=[CH:10][CH2:9][C:6]2([CH2:7][CH2:8]2)[C@H:5]1[C:12](=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 68723299HCID 68723299, compound

Product 1

HCID 68773599HCID 68773599, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
80 °C

Procedure

Na (22.7 mg, 0.987 mmol) was added to MeOH (24 ml). The resulting solution was treated at 25° C. with rel-(4R,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone (1.62 g, 9.97 mmol, prepared in example 11), and heated at 80° C. for 64 h. The resulting solution was cooled, diluted pentane and poured into a saturated aqueous NH4Cl solution. The aqueous phase was extracted twice with pentane and the combined organic phases were washed with a saturated aqueous NaCl solution, dried (Na2SO4) and concentrated. FC (250 g SiO2, pentane/Et2O 10:0.5) of the crude product (1.5 g) gave rel-(4S,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone (930 mg, 57%) and a rel-(4R,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone/rel-(4S,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone (60:40, 408 mg, 25%).

Workup

  1. temperatureThe resulting solution was cooled
  2. extractionThe aqueous phase was extracted twice with pentane
  3. washthe combined organic phases were washed with a saturated aqueous NaCl solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3257d533af8540799c5a1991ffb7ecc9
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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