4H-1-Benzopyran-2-carboxylic acid, 4-oxo-, methyl ester → Methyl 3,4-dihydro-2H-1-benzopyran-2-carboxylate

HRID 984101Notes

Reaction equation

HRID 984101 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]([C:12]([O:14][CH3:15])=[O:13])=[CH:3]1.COC(C1CCC2C(=CC=C(S(Cl)(=O)=O)C=2)O1)=O>[Pd]>[CH3:15][O:14][C:12]([CH:4]1[CH2:3][CH2:2][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5]1)=[O:13]

Participants

4

Reactant 2

HCID 290574H-1-Benzopyran-2-carboxylic acid, 4-oxo-, methyl esterHCID 23567177HCID 23567177, compound2×

Product 1

HCID 14838439Methyl 3,4-dihydro-2H-1-benzopyran-2-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Compound 3A was prepared by hydrogenation of the methyl 4-oxo-4H-chromene-2-carboxylate catalyzed by 10% Pd/C in 93% yield. MS: MS: 193 (M+1)+. Preparation of 6-Chlorosulfonyl-chroman-2-carboxylic acid methyl ester (Compound 3B)

Sources & evidence

ORD record
ord-5eb2bf08cb4a45bc9e728fd87e6b006c
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

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