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

HRID 461552

반응식

HRID 461552 반응식
[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

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 8857Ethyl AcetateHCID 128917863-(Dimethylamino)-6-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazoleHCID 21226445Aluminium lithium hydride

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eed915d4159a4ac489052b6a01448978
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04062864

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