Methyl Ethyl Ketone → Methyl 7-(3-chloropropoxy)-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate

HRID 1033633Notes

Reaction equation

HRID 1033633 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[CH2:6][CH2:7][CH:8]([C:10]([O:12][CH3:13])=[O:11])[O:9][C:4]=2[C:3]=1[CH2:16][CH2:17][CH3:18].Br[CH2:20][CH2:21][CH2:22][Cl:23].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>C(OCC)(=O)C>[Cl:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:15]=[CH:14][C:5]2[CH2:6][CH2:7][CH:8]([C:10]([O:12][CH3:13])=[O:11])[O:9][C:4]=2[C:3]=1[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 13537867Methyl 3,4-dihydro-7-hydroxy-8-propyl-2H-1-benzopyran-2-carboxylate

Product 1

HCID 14722827Methyl 7-(3-chloropropoxy)-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3,4-dihydro-7-hydroxy-8-propyl-2H-1-benzopyran-2-carboxylate (10 g, 40 mmol), 1-bromo-3-chloropropane (75 g, 48 mmol), and potassium carbonate (828 g, 60 mmol) were added to 100 ml of methyl ethyl ketone, and the reaction mixture was heated to reflux and stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, concentrated, and the crude product was chromatographed on silica gel using 20% ethyl acetate/80% hexane as eluant to give the product.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe crude product was chromatographed on silica gel using 20% ethyl acetate/80% hexane as eluant
  7. customto give the product

Sources & evidence

ORD record
ord-397e5e51548446329eaeb78aa3199de3
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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