Ethyl Acetate → HCID 15617906, compound

HRID 1165018Notes

Reaction equation

HRID 1165018 reaction equation
[C:1]1([CH2:7][C:8]2[CH:9]=[C:10]([C:20]([OH:22])=[O:21])[C:11]3[C:16]([C:17]=2[O:18]C)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23](OCC)(=O)[CH3:24]>S(=O)(=O)(O)O.C(O)C.O>[CH2:23]([O:22][C:20]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=1)=[O:21])[CH3:24]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 15617904HCID 15617904, compound

Product 1

HCID 15617906HCID 15617906, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of the compound of Example 95 (2.55 g, 9.2 mmole) and concentrated sulfuric acid (3 drops) in ethanol (125 mL) was heated at reflux for 80 hours. The mixture was cooled and diluted with water, and the crude product was isolated by extraction with ethyl acetate. This was chromatographed (9:1 hexane/ethyl acetate) and recrystallized (hexane) to provide the title compound (1.74 g, 62%) as white needles, mp 79°-80°.

Workup

  1. temperatureat reflux for 80 hours
  2. temperatureThe mixture was cooled
  3. customThis was chromatographed (9:1 hexane/ethyl acetate)
  4. customrecrystallized (hexane)

Sources & evidence

ORD record
ord-cf46cbc2985b47f5b05491845bb6b4bf
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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