Ethanol → HCID 9867769, compound

HRID 275375Notes

Reaction equation

HRID 275375 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10]2[CH:25]=[CH:24][C:13]3[C:14](=[O:23])[CH:15]=[C:16]([C:18]([O:20]CC)=[O:19])[O:17][C:12]=3[C:11]=2[CH2:26][CH2:27][CH3:28])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].C(O)C>O>[C:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10]2[CH:25]=[CH:24][C:13]3[C:14](=[O:23])[CH:15]=[C:16]([C:18]([OH:20])=[O:19])[O:17][C:12]=3[C:11]=2[CH2:26][CH2:27][CH3:28])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 15682677HCID 15682677, compound

Product 1

HCID 9867769HCID 9867769, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.6 g. of the ethyl ester from Example 1 and 4.5 g. of sodium bicarbonate was heated to reflux in 100 ml. of ethanol and 25 ml. of water for four hours. The solution was then concentrated under reduced pressure. The residue was taken up in water. The solution was made acidic with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate was washed with water, dried over sodium sulfate, and evaporated to dryness. The residue was crystallized from ethanol/water to afford 0.2 g. of the desired title product, m.p. 195°-205° C.

Workup

  1. temperatureto reflux in 100 ml
  2. concentrationThe solution was then concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was crystallized from ethanol/water
  8. customto afford 0.2 g

Sources & evidence

ORD record
ord-7ac0122ab5ed403fa82d22dfcc30f448
Source dataset
uspto-grants-1995_02
Patent number
US05393768

Reaction notes

Loading…