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

HRID 464014Notes

Reaction equation

HRID 464014 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].[Na]>CC(C)=O>[CH2:3]([O:4][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])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:21][CH2:20][CH3:19]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 131462679(R)-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Product 1

HCID 132929979(R)-octyloxyacetyl-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 octate (4.8 g) and acetone (50 ml) was stirred under reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was triturated with addition of ether (15 ml). Solid substances were filtered to give orange crystals of 9(R)-octyloxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione. M.P., 144°-148° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with addition of ether (15 ml)
  4. filtrationSolid substances were filtered

Sources & evidence

ORD record
ord-b6afed906e4f41c78a2df7c6519c12d9
Source dataset
uspto-grants-1985_10
Patent number
US04545936

Reaction notes

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