HCID 22313309, compound → Methyl 3,4-dihydro-2H-1-benzopyran-7-carboxylate

HRID 965840Notes

Reaction equation

HRID 965840 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH2:2]1.[H][H]>CO.[Pd]>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 22313309HCID 22313309, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22313392Methyl 3,4-dihydro-2H-1-benzopyran-7-carboxylateYield 37.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2H-chromene-7-carboxylate (372 mg, 1.96 mmol) and 10% Pd/C (25 mg) in methanol (15 mL) is stirred under 1 atm of hydrogen at rt for 3 h. The mixture is filtered through Celite and the filtrate is concentrated to a yellow residue. The crude product is purified by flash chromatography on SiO2. Elution with hexanes-EtOAc (95:5) gives 140 mg (37%) of methyl chromane-7-carboxylate as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.51, 7.47, 7.10, 4.23, 3.91, 2.85, 2.04.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated to a yellow residue
  3. customThe crude product is purified by flash chromatography on SiO2
  4. washElution with hexanes-EtOAc (95:5)

Sources & evidence

ORD record
ord-0a502fa381df4f06bc74553384e54ea4
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

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