Acetonitrile → HCID 56612709, compound

HRID 1252985Notes

Reaction equation

HRID 1252985 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH3:14].C([O-])(=O)C.[Na+].C(#N)C>O>[CH3:14][C:4]1[C:3](=[O:2])[CH:8]=[C:7]([CH2:9][OH:10])[C:6](=[O:11])[C:5]=1[CH3:13]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 517045Sodium AcetateHCID 20137829HCID 20137829, compound

Product 1

HCID 56612709HCID 56612709, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of intermediate E (1.8 g, 9 mmole), sodium acetate (7.5 g, 91 mmole), acetonitrile (134 ml) and water (29 ml), silver dipicolinate complex (19.2 g, 44 mmole, prepared by the method described by K. Kloc et al in Chem. Lett., 725. 1980) was added slowly with vigorous stirring over 30 minutes at room temperature. The mixture was stirred over 30 minutes longer, water (150 ml) was added, and the silver salts were filtered off and washed with chloroform. The filtrate was extracted several times with chloroform. The combined extracts were dried, concentrated to a small volume and chromatographed (silica, dichloromethane:ethyl acetate, 95:5). There was obtained 900 mg of ETA I, mp 71°-72° C. Calculated elemental analysis for C9H10O3 is C, 65.1, H, 6.1, and 0, 28.9. Elemental analysis found was C, 64.9, H, 5.9, and 0, 28.7.

Workup

  1. customprepared by the method
  2. addition1980) was added slowly
  3. stirringThe mixture was stirred over 30 minutes longer
  4. filtrationthe silver salts were filtered off
  5. washwashed with chloroform
  6. extractionThe filtrate was extracted several times with chloroform
  7. customThe combined extracts were dried
  8. concentrationconcentrated to a small volume
  9. customchromatographed (silica, dichloromethane:ethyl acetate, 95:5)
  10. customThere was obtained 900 mg of ETA I, mp 71°-72° C

Sources & evidence

ORD record
ord-9e37c8123a7e4be69acc3f350aba7775
Source dataset
uspto-grants-1988_05
Patent number
US04746607

Reaction notes

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