5-Benzyloxy-4-t-butyl-2-formylbenzofuran → 4-Tert-butyl-5-hydroxy-2-hydroxymethyl-2,3-dihydrobenzofuran

HRID 1376965Notes

Reaction equation

HRID 1376965 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]=[O:18])=[CH:14][C:13]=2[C:19]=1[C:20]([CH3:23])([CH3:22])[CH3:21])C1C=CC=CC=1>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[C:20]([C:19]1[C:13]2[CH2:14][CH:15]([CH2:17][OH:18])[O:16][C:12]=2[CH:11]=[CH:10][C:9]=1[OH:8])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 1

HCID 234428795-Benzyloxy-4-t-butyl-2-formylbenzofuran

Product 1

HCID 229186574-Tert-butyl-5-hydroxy-2-hydroxymethyl-2,3-dihydrobenzofuranYield 87.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Benzyloxy-4-tert-butyl-2-formylbenzofuran (5.0 g, 16 mmol) was dissolved in a 25:1 mixed solution (260 ml) of ethyl acetate and acetic acid. After adding 10% Pd on carbon (5.0 g), the solution was stirred under a hydrogen atmosphere for 48 h. After filtering off the Pd on carbon, the filtrate was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was subjected to silica gel chromatography and eluted with a solvent system consisting of a 4:1 mixture of hexane and ethyl acetate to afford 4-tert-butyl-5-hydroxy-2-hydroxymethyl-2,3-dihydrobenzofuran [3.1 g (yield, 87%)] as a colorless oil.

Workup

  1. filtrationAfter filtering off the Pd on carbon
  2. washthe filtrate was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with a solvent system
  6. additionconsisting of a 4:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-3212ad0201ad4d258b08b0cd179717f7
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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