Hydrochloric Acid → HCID 53996178, compound

HRID 2231907Notes

Reaction equation

HRID 2231907 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1([CH3:28])[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([C:25](=[O:27])[CH3:26])[C:15]([O:20][CH2:21][CH2:22][CH2:23]Br)=[C:16]([CH2:17][CH2:18][CH3:19])[C:9]=2[O:8]1)[CH3:2].[OH:30][C:31]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35]([OH:40])[CH:34]=[CH:33][C:32]=1[C:41](=[O:43])[CH3:42].C(=O)([O-])[O-].[K+].[K+].Cl>CCOCC.O.CN(C)C=O.CC(C)=O>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1([CH3:28])[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([C:25](=[O:27])[CH3:26])[C:15]([O:20][CH2:21][CH2:22][CH2:23][O:40][C:35]3[CH:34]=[CH:33][C:32]([C:41](=[O:43])[CH3:42])=[C:31]([OH:30])[C:36]=3[CH2:37][CH2:38][CH3:39])=[C:16]([CH2:17][CH2:18][CH3:19])[C:9]=2[O:8]1)[CH3:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 54439247HCID 54439247, compound

Product 1

HCID 53996178HCID 53996178, compoundYield 52.7%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 335 mg of racemic-6-acetyl-7-(3-bromopropoxy)-3,4-dihydro-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester, 143 mg of 2',4'-dihydroxy-3'-n-propylacetophenone, 217 mg of anhydrous potassium carbonate, 6 ml of anhydrous acetone, and 3 ml of anhydrous N,N-dimethylformamide was stirred and refluxed for 17 hours. An additional 100 mg of potassium carbonate was added and stirring, and refluxing were continued for 4 hours. After being cooled to room temperature, the mixture was cautiously acidified to pH 1 by the addition of 1N hydrochloric acid. Water was added and the mixture was worked-up with ether in the usual manner. The residue was chromatographed on 50 g of silica gel. Elution with 9:1 toluene-ethyl acetate afforded 219 mg (52.6%) of racemic-6-acetyl-7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3,4-dihydro-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester as a yellow oil.

Workup

  1. temperaturerefluxed for 17 hours
  2. stirringstirring
  3. temperaturerefluxing
  4. customThe residue was chromatographed on 50 g of silica gel
  5. washElution with 9:1 toluene-ethyl acetate

Sources & evidence

ORD record
ord-612bbc1492ec4bbb956f3545f86e3cae
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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