HCID 18694144, compound → HCID 18694185, compound

HRID 1870982Notes

Reaction equation

HRID 1870982 reaction equation
O=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]3[CH2:14][CH2:13][CH2:12][C:11]=3[C:6]=2[O:5][C:4]([C:15]([OH:17])=[O:16])=[CH:3]1.[H][H]>C(O)(=O)C.[Pd]>[O:5]1[C:6]2[C:11]3[CH2:12][CH2:13][CH2:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH2:2][CH2:3][CH:4]1[C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 18694144HCID 18694144, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18694185HCID 18694185, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of intermediate (3-a) (0.09 mol) in acetic acid (200 ml) was hydrogenated with palladium on activated carbon (1 g) as a catalyst. After uptake of hydrogen (3 eq.), the catalyst was filtered off. The solvent was evaporated. The residue was vacuum dried, yielding 21 g of (±)-2,3,4,7,8,9-hexahydrocyclopenta[h]-1-benzopyran-2-carboxylic acid (interm. 4-a).

Workup

  1. customThe solvent was evaporated
  2. customdried

Sources & evidence

ORD record
ord-6c314a6f61ee47f09b5cef5ece73955d
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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