Acetic Acid → diethyl 6-acetyl-3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

HRID 2371652Notes

Reaction equation

HRID 2371652 reaction equation
[CH2:1]([C:4]1[C:13]2[O:12][C:11]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[OH:28])[CH2:2][CH3:3].[C:29](O)(=[O:31])[CH3:30]>[Cl-].[Zn+2].[Cl-]>[C:29]([C:6]1[C:5]([OH:28])=[C:4]([CH2:1][CH2:2][CH3:3])[C:13]2[O:12][C:11]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][CH2:9][C:8]=2[CH:7]=1)(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 15157486diethyl 3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

Product 1

HCID 15157494diethyl 6-acetyl-3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a solution of 790 mg (2.01 mmol) of the title product of Example 44 in 4 ml of acetic acid was added 547 mg (4.02 mmol) of anhydrous zinc chloride. The mixture was stirred for six hours at reflux, and then permitted to cool. The mixture was partitioned between ethyl acetate and dilute hydrochloric acid. The aqueous layer was further extracted with two portions of ethyl acetate. The combined organic extracts were washed successively with five portions of aqueous sodium bicarbonate, water, and then brine. The extracts were dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. Chromatography of the residue over silica gel using 25% ethyl acetate/hexane as eluent gave the title compound, 230 mg.

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. customThe mixture was partitioned between ethyl acetate and dilute hydrochloric acid
  4. extractionThe aqueous layer was further extracted with two portions of ethyl acetate
  5. washThe combined organic extracts were washed successively with five portions of aqueous sodium bicarbonate, water
  6. dry with materialThe extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-843ce68f4a4c4bccb551b0af42613444
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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