Sodium Methoxide → HCID 58158112, compound

HRID 1255507Notes

Reaction equation

HRID 1255507 reaction equation
C([O:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14])(=O)C.C[O-].[Na+]>CO>[CH2:10]([C@@H:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[OH:4])[CH2:11][CH2:12][CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58158116HCID 58158116, compound

Product 1

HCID 58158112HCID 58158112, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A stirred solution of (1R,2R)-2-pent-4-en-1-ylcyclopentyl acetate (3.79 g, 19.3 mmol) in MeOH (320 ml) was treated with methanolic NaOMe (25%, 8.1 ml, 35.4 mmol) and stirred for 15 hours at 20° C. DOWEX 50WX8-100 ion-exchange resin (washed with MeOH) was added portionwise until the pH was neutral, then the mixture was filtered through CELITE. The filtrate was concentrated in vacuo, and the residue was partitioned between EtOAc and H2O. The organic layer was separated, washed with brine, and dried over Na2SO4. Filtration and removal of the volatiles afforded the title compound (2.61 g, 88%) as a liquid that was used directly in the subsequent reactions. [α]D −37.3 (c=0.65, CHCl3).

Workup

  1. washion-exchange resin (washed with MeOH)
  2. additionwas added portionwise until the pH
  3. filtrationthe mixture was filtered through CELITE
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was partitioned between EtOAc and H2O
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationFiltration and removal of the volatiles

Sources & evidence

ORD record
ord-e6b51d653c984f15a058a113cb203ebb
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

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