Ethyl acetate hexane → HCID 22161963, compound
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
Product 1
Reagents, catalysts & solvents 2
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
- customthe reaction
- filtrationThe catalyst was filtered off through a celite pad
- concentrationthe filtrate concentrated down
- customto afford 96 mg crude product as an oil
- 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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