Indole → 6-(1H-indol-3-yl)hexanoic acid

HRID 346793

반응식

HRID 346793 반응식
O.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[C:11]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[OH-].[K+]>CC1C=CC(C(C)C)=CC=1>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:11]([OH:18])=[O:17])=[CH:3]1

참가 물질

6

반응물 4

HCID 798IndoleHCID 962Water2회HCID 10401epsilon-CAPROLACTONEHCID 14797Potassium Hydroxide

생성물 1

HCID 46727896-(1H-indol-3-yl)hexanoic acid

시약·촉매·용매 1

HCID 7463P-Cymene용매

실험 절차

In a water separator, indole (50 g, 0.43 mol.), ε-caprolactone (oxepan-2-one, 55.9 g, 0.49 mol.), potassium hydroxide (35.9 g, 0.64 mol.) in p-cymene (1-isopropyl-4-methylbenzene, 250 ml) were heated at boiling for 4 d, with stirring. For working up, water (200 ml) was added to the mixture, the phases were separated, and the aqueous phase was adjusted to pH 4 with 2M HCl and stored for 2 d at 4° C. in a refrigerator. The resulting solid was filtered off with suction and washed with water (3×20 ml). Recrystallisation from ether (50 ml) yielded 6-(1H-indol-3-yl)hexanoic acid in the form of a white solid having a melting point of 124–126° C. in a yield of 16.9 g.

후처리

  1. customthe phases were separated
  2. waitstored for 2 d at 4° C. in a refrigerator
  3. filtrationThe resulting solid was filtered off with suction
  4. washwashed with water (3×20 ml)
  5. customRecrystallisation from ether (50 ml)

출처 및 근거

ORD 기록
ord-ada1d4d81014435da937c72e3ca1084d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173045B2

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