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

HRID 128111

反応式

HRID 128111 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-479a7443281d4398b971fe7dbcf7f924
出典データセット
uspto-grants-1981_03
特許番号
US04257952

関連ノート

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