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

HRID 867171Notes

Reaction equation

HRID 867171 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 5B 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 (5C), as a yellow liquid, boiling point not determined.

Workup

  1. filtrationThe reaction mixture then was filtered

Sources & evidence

ORD record
ord-b670f06f04e546718ed449c6b49d6660
Source dataset
uspto-grants-1978_07
Patent number
US04103021

Reaction notes

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