Ethyl acetate hexane → HCID 22161963, compound

HRID 1088727Notes

Reaction equation

HRID 1088727 reaction equation
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]2[CH2:8][CH2:9][S:10][C:6]=2[CH:5]=1)[CH:2]=[CH2:3].CCCCCC.CCOC(C)=O>C(O)C.[Pd]>[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]2[CH2:8][CH2:9][S:10][C:6]=2[CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 22161965HCID 22161965, compound

Product 1

HCID 22161963HCID 22161963, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-allyl-2,3-dihydrobenzothiophene (95 mg, 0.49 mmole) in 10 mL absolute ethanol was hydrogenated at 40 psi over 20 mg 10% Pd/C at room temperature overnight. TLC (90/10, hexane/EtOAc) indicated the reaction to be complete. The catalyst was filtered off through a celite pad and the filtrate concentrated down to afford 96 mg crude product as an oil. Purification by flash chromatography (90/10, hexane/EtOAc) afforded 75 mg white solids mp 58°-60° C. (78%).

Workup

  1. customthe reaction
  2. filtrationThe catalyst was filtered off through a celite pad
  3. concentrationthe filtrate concentrated down
  4. customto afford 96 mg crude product as an oil
  5. customPurification by flash chromatography (90/10, hexane/EtOAc)

Sources & evidence

ORD record
ord-840ed4cbd7704e2b8c2f736bd95d9421
Source dataset
uspto-grants-1990_10
Patent number
US04963580

Reaction notes

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