methyl 6-chloro-2H-chromene-3-carboxylate → Methyl 6-chloro-3,4-dihydro-2H-1-benzopyran-3-carboxylate
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]=1Participants
5
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
- 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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