Tetrahydrofuran → 3-(Dimethylamino)-6-hydroxymethyl-1,2,3,4-tetrahydrocarbazole

HRID 461552

Reaction equation

HRID 461552 reaction equation
[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16](OCC)=[O:17])[CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O>[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([CH2:16][OH:17])[CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 128917863-(Dimethylamino)-6-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 128918673-(Dimethylamino)-6-hydroxymethyl-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 12.8 g. of 3-(dimethylamino)-6-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole (Example 43) in 350 ml. of dry tetrahydrofuran was added dropwise to a refluxing solution of 3.5 g. of lithium aluminum hydride in 100 ml. of dry tetrahydrofuran and refluxing was continued for one hour after completion of the addition. Ethyl acetate was added followed by water, the mixture was filtered, and the filtrate was evaporated to dryness to give, after recrystallization from ethyl alcohol, 6.4 g. of 3-(dimethylamino)-6-hydroxymethyl1,2,3,4-tetrahydrocarbazole, m.p. 195°-197° C.

Workup

  1. additionafter completion of the addition
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. customto give
  5. customafter recrystallization from ethyl alcohol, 6.4 g

Sources & evidence

ORD record
ord-eed915d4159a4ac489052b6a01448978
Source dataset
uspto-grants-1977_12
Patent number
US04062864

Linked notes

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