Potassium Carbonate → diethyl 3,4-dihydro-7-(3-phenoxypropoxy)-8-propyl-2H-1-benzopyran-2,2-dipropanoate

HRID 2371636Notes

Reaction equation

HRID 2371636 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].Br[CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:33]([CH2:32][CH2:31][CH2:30][O:28][C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][CH2:10][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])[O:12][C:13]=2[C:4]=1[CH2:1][CH2:2][CH3:3])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 15157486diethyl 3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

Product 1

HCID 15157492diethyl 3,4-dihydro-7-(3-phenoxypropoxy)-8-propyl-2H-1-benzopyran-2,2-dipropanoateYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 370 mg (0.941 mmol) of the title product of Example 44, 243 mg (1.13 mmol) of 1-bromo-3-phenoxypropane, and 273 mg (1.98 mmol) of anhydrous potassium carbonate in 10 ml of dimethylformamide was stirred overnight at room temperature. Thereafter, the solvent was removed under reduced pressure, and the residue was partitioned between ethyl acetate and water. The aqueous layer was separated, acidified with 3N hydrochloric acid, and the layers reshaken. The aqueous layer was further extracted with two portions of ethyl acetate. The combined organic extracts were dried over magnesium sulfate, and the solvent was removed under reduced pressure. The title compound (185 mg) was obtained after chromatography on silica gel using 20% ethyl acetate/hexane as eluent.

Workup

  1. customThereafter, the solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe aqueous layer was separated
  4. extractionThe aqueous layer was further extracted with two portions of ethyl acetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-06419073742a4d1295cccf3c1377382d
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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