Sodium Hydroxide → 9-(2-Benzyloxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid

HRID 1753934노트

반응식

HRID 1753934 반응식
C([O:3][C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[CH2:22]([O:21][CH2:20][CH2:19][N:11]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 666793589-(2-Benzyloxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester

생성물 1

HCID 666795949-(2-Benzyloxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid수율 92%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

9-(2-Benzyloxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester (25) (35 g, 9.3 mmol) was dissolved in ethanol (9 mL) and then NaOH (1.56 g) in water (15 mL) was added. The reaction was heated at reflux for 2 h. The reaction was concentrated in vacuo and the residue diluted with water and washed with dichloromethane (2×150 mL). The aqueous layer was added drop wise to 2 N HCl (150 mL) and then extracted into dichloromethane (3×150 mL). The organics were dried and concentrated in vacuo to afford 2.48 g (92%) of 9-(2-benzyloxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid (26) as a yellow solid which was used in the next step without purification. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 20.4, 21.8, 26.4, 38.3, 42.9, 68.7, 73.3, 105.7, 108.8, 118.7, 119.3, 102.9, 127.4, 127.6, 128.3, 136.2, 137.1, 137.8, 108.9.

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction was concentrated in vacuo
  4. additionthe residue diluted with water
  5. washwashed with dichloromethane (2×150 mL)
  6. additionThe aqueous layer was added drop wise to 2 N HCl (150 mL)
  7. extractionextracted into dichloromethane (3×150 mL)
  8. customThe organics were dried
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c40c30caafcf4e998ef451de9cfe6eb2
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09168317B2

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