Potassium Carbonate → diethyl 6-acetyl-3,4-dihydro-8-propyl-7-[3-[(5,6,7,8-tetrahydro-1-naphthalenyl)oxy]propoxy]-2H-1-benzopyran-2,2-dipropanoate

HRID 2371653Notes

Reaction equation

HRID 2371653 reaction equation
[C:1]([C:4]1[C:5]([OH:31])=[C:6]([CH2:28][CH2:29][CH3:30])[C:7]2[O:12][C:11]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9][C:8]=2[CH:27]=1)(=[O:3])[CH3:2].[C:32]1([O:42][CH2:43][CH2:44][CH2:45]Br)[C:41]2[CH2:40][CH2:39][CH2:38][CH2:37][C:36]=2[CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([C:4]1[C:5]([O:31][CH2:45][CH2:44][CH2:43][O:42][C:32]2[C:41]3[CH2:40][CH2:39][CH2:38][CH2:37][C:36]=3[CH:35]=[CH:34][CH:33]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:7]2[O:12][C:11]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9][C:8]=2[CH:27]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 144059475-(3-Bromopropoxy)-1,2,3,4-tetrahydronaphthaleneHCID 15157494diethyl 6-acetyl-3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

Product 1

HCID 15157495diethyl 6-acetyl-3,4-dihydro-8-propyl-7-[3-[(5,6,7,8-tetrahydro-1-naphthalenyl)oxy]propoxy]-2H-1-benzopyran-2,2-dipropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 204 mg (0.469 mmol) of the title product of Example 81, 378 mg (1.41 mmol) of the title product of Example 12, and 136 mg (0.985 mmol) of anhydrous potassium carbonate in 4 ml of dimethylformamide was stirred at 80° for six hours. A further 136 mg of potassium carbonate was added, and the mixture was heated for another six hours. The mixture was permitted to cool and 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 with brine, dried over sodium sulfite, filtered, and the solvent removed under reduced pressure. Chromotography of the residue over silica gel using 15% ethyl acetate/toluene as eluent gave the title compound, 114 mg.

Workup

  1. temperaturethe mixture was heated for another six hours
  2. temperatureto cool
  3. customwas 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 with brine
  6. dry with materialdried over sodium sulfite
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-443f29d2886b4b958fc87c4b098f7cce
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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