Methane → HCID 11386963, compound

HRID 600996Notes

Reaction equation

HRID 600996 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[CH:26]=1)C1C=CC=CC=1.C.[H][H]>C(O)C.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[CH:26]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 67062373HCID 67062373, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11386963HCID 11386963, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(16-benzyloxyhexadecenyl)-1-(4-methoxybenzensulfonyl)indole (530 mg, 0.86 mmol) was dissolved in 25 mL of ethanol and added to palladium supported on activated charcoal (5%, 50 mg). The resulting mixture was allowed to stand at room temperature for 3 hours under 1 atmospheric pressure of hydrogen. After filtration, the reaction mixture was extracted with ethyl ether. The organic layer was concentrated under reduced pressure. The residue was purified by flash chromatography to give 3-(16-hydroxyhexadecyl)-1-(4-methoxybenzenesulfonyl)indole as a white solid (417 mg, 92%).

Workup

  1. filtrationAfter filtration
  2. extractionthe reaction mixture was extracted with ethyl ether
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3b2eab01256a48059779464a9e1b3654
Source dataset
uspto-grants-2011_03
Patent number
US07902249B2

Reaction notes

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