Ethyl acetate hexane → HCID 11187199, compound

HRID 430756Notes

Reaction equation

HRID 430756 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[CH:7][C:8]1[O:9][C:10]2[C:25]([O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=[CH:22][C:11]=2[C:12]=1[CH2:13][CH2:14][O:15]C1CCCCO1)(=[O:3])[CH3:2].CCCCCC.C(OCC)(=O)C>CO.[Pd]>[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]2[C:25]([O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=[CH:22][C:11]=2[C:12]=1[CH2:13][CH2:14][OH:15])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 53638626HCID 53638626, compound

Product 1

HCID 11187199HCID 11187199, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl (2-(3-acetoxy-1-propenyl)-3-(2-tetrahydropyranyloxyethyl)benzofuran-7-yloxy)acetate (199 mg) was dissolved in methanol (4 ml) and 5% Pd/C (28 mg) was added to the solution, followed by stirring the solution at room temperature for 1.5 hours under hydrogen atmosphere. After filtering the reaction solution through Celite, the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1)using silica gel to obtain the desired compound (80 mg, yield: 50%).

Workup

  1. filtrationAfter filtering the reaction solution through Celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography (solvent

Sources & evidence

ORD record
ord-8342bdcbc4ad4bec9b8417fce6033237
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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