Acetone → HCID 54439247, compound

HRID 2231906Notes

Reaction equation

HRID 2231906 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7]1([CH3:24])[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([C:21](=[O:23])[CH3:22])[C:15]([OH:20])=[C:16]([CH2:17][CH2:18][CH3:19])[C:9]=2[O:8]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:32][CH2:33][CH2:34][CH2:35]Br.CC(C)=O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7]1([CH3:24])[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([C:21](=[O:23])[CH3:22])[C:15]([O:20][CH2:35][CH2:34][CH2:33][Br:32])=[C:16]([CH2:17][CH2:18][CH3:19])[C:9]=2[O:8]1)[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate2×HCID 54226052HCID 54226052, compound

Product 1

HCID 54439247HCID 54439247, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 263 mg of racemic-6-acetyl-3,4-dihydro-7-hydroxy-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester, 222 mg of anhydrous potassium carbonate, 0.39 ml of 1,3-dibromopropane, 6 ml of anhydrous acetone, and 3 ml of anhydrous N,N-dimethylformamide was stirred and refluxed for 16 hours. An additional 0.25 g of anhydrous potassium carbonate was added and stirring, and refluxing were continued for 25 hours. The mixture was cooled and volatile materials were removed first under water aspirator pressure and then high vacuum. The residue was treated with ether and acetone and the solids were removed by filtration. Concentration of the filtrate in vacuo afforded 359 mg of racemic-6-acetyl-7-(3-bromopropoxy)-3,4-dihydro-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester as an orange oil.

Workup

  1. temperaturerefluxed for 16 hours
  2. stirringstirring
  3. temperaturerefluxing
  4. temperatureThe mixture was cooled
  5. customvolatile materials were removed first under water aspirator pressure
  6. additionThe residue was treated with ether and acetone
  7. customthe solids were removed by filtration

Sources & evidence

ORD record
ord-97c824ad6197427581c0253e88a17d98
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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