Sodium Valerate → 9(R)-valeryloxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

HRID 464015Notes

Reaction equation

HRID 464015 reaction equation
Br[CH2:2][C:3]([C@:5]1([OH:27])[CH2:22][C:21]2[C:20]([OH:23])=[C:19]3[C:10]([C:11](=[O:25])[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:18]3=[O:24])=[C:9]([OH:26])[C:8]=2[CH2:7][CH2:6]1)=[O:4].[C:28]([O-:34])(=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32].[Na+]>CC(C)=O>[C:28]([O:34][CH2:2][C:3]([C@:5]1([OH:27])[CH2:22][C:21]2[C:20]([OH:23])=[C:19]3[C:10]([C:11](=[O:25])[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:18]3=[O:24])=[C:9]([OH:26])[C:8]=2[CH2:7][CH2:6]1)=[O:4])(=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 3669864Sodium ValerateHCID 131462679(R)-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Product 1

HCID 132929949(R)-valeryloxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9(R)-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (1.00 g) obtained in Reference Example 4-(1), sodium valerate (1.44 g) and acetone (50 ml) was stirred under reflux for 2 hours. After removing insoluble matters by filtration, the reaction mixture was concentrated under reduced pressure. The residue was treated with ether (15 ml) and precipitated crystals were collected by filtration to give orange crystals of 9(R)-valeryloxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione. M.P., 149°-152° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customAfter removing insoluble matters
  3. filtrationby filtration
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionThe residue was treated with ether (15 ml)
  6. customprecipitated crystals
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-c0125d953c224046aa51d26fc3ec806d
Source dataset
uspto-grants-1985_10
Patent number
US04545936

Reaction notes

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