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

HRID 427148

Reaction equation

HRID 427148 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-hydroxymethyl-1,2,3,4-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-c729dad9263e43249e9fd97ec37982f4
Source dataset
uspto-grants-1979_10
Patent number
US04172834

Linked notes

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