Benzene → N-[(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]-acetamide

HRID 1660333Notes

Reaction equation

HRID 1660333 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1.C[CH:14]([NH:18][C:19](=[O:21])[CH3:20])[C:15](=O)[CH3:16].[CH:22]1C=CC=CC=1>B(F)(F)F.CCOCC>[CH3:22][C:16]1([CH2:15][CH2:14][NH:18][C:19](=[O:21])[CH3:20])[C:2]2[NH:1][C:9]3[C:4]([C:3]=2[CH2:10][CH2:11][O:12]1)=[CH:5][CH:6]=[CH:7][CH:8]=3

Participants

5

Reactant 3

HCID 241BenzeneHCID 10685TryptopholHCID 97923N-(1-methyl-2-oxopropyl)acetamide

Product 1

HCID 54536583N-[(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateCatalyst

Procedure

A mixture of indole-3-ethanol (16 lg), benzene (1200 ml), N-(1-methyl-2-oxopropyl)-acetamide[12.7 g, described by A. Triebs and W. Sutter, Chem. Ber. 84, 96(1951)] and boron trifluoride-etherate (5 drops) is refluxed using a water separating condenser for 60 minutes. After cooling, the mixture is washed with concentrated sodium bicarbonate, dried over magnesium sulfate and evaporated. The residue is chromatographed on silica gel using chloroform. The eluates are evaporated to give a residue of the title compound as a 1:1 mixture of diastereoisomers:

Workup

  1. customfor 60 minutes
  2. temperatureAfter cooling
  3. washthe mixture is washed with concentrated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel
  7. customThe eluates are evaporated

Sources & evidence

ORD record
ord-1b0255e2d88346bf93dff6dbcfc7eebf
Source dataset
uspto-grants-1981_12
Patent number
US04307234

Reaction notes

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