methyl 6-chloro-2H-chromene-3-carboxylate → Methyl 6-chloro-3,4-dihydro-2H-1-benzopyran-3-carboxylate

HRID 1447792Notes

Reaction equation

HRID 1447792 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:6]=2[CH:15]=1.[H][H]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][C:6]=2[CH:15]=1

Participants

5

Reactant 2

HCID 2763891methyl 6-chloro-2H-chromene-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 20383065Methyl 6-chloro-3,4-dihydro-2H-1-benzopyran-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

700 mg of 6B was dissolved in 75 ml of ethyl acetate and the solution was treated with hydrogen (initial pressure of 30 psig), in the presence of a 10% palladium-on-carbon catalyst, for 8 hours. The reaction mixture then was filtered and stripped of solvent to give methyl 6-chloro-3,4-dihydro-2H-1-benzopyran-3-carboxylate (6C), as a yellow liquid, boiling point not determined.

Workup

  1. filtrationThe reaction mixture then was filtered

Sources & evidence

ORD record
ord-48dc98b57d864474931373062465d6e6
Source dataset
uspto-grants-1979_12
Patent number
US04178380

Reaction notes

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