HCID 86586188, compound → HCID 12094377, compound

HRID 2119705Notes

Reaction equation

HRID 2119705 reaction equation
[C:1]([C:5]1[C:19]([OH:20])=[C:18]([CH2:21][CH:22]=[CH2:23])[C:8]2[CH2:9][C:10]3([O:17][C:7]=2[CH:6]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:5]1[C:19]([OH:20])=[C:18]([CH2:21][CH2:22][CH3:23])[C:8]2[CH2:9][C:10]3([O:17][C:7]=2[CH:6]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86586188HCID 86586188, compound

Product 1

HCID 12094377HCID 12094377, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.51 g of 6-t-butyl-5-hydroxy-4-(2-propenyl)-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane synthesized in Example 8 was dissolved in 5 ml of ethanol and the solution was vigorously stirred with 0.05 g of 10% palladium on carbon overnight under a hydrogen stream. After the palladium on carbon was filtered off, the mixture was concentrated and the concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate) to give 0.49 g of 6-t-butyl-5-hydroxy-4-n-propyl-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane as a white solid (yield 95%).

Workup

  1. filtrationAfter the palladium on carbon was filtered off
  2. concentrationthe mixture was concentrated
  3. customthe concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate)

Sources & evidence

ORD record
ord-1e5c2493919243ac8284681308c777d7
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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