Water → 4-[(2-Ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acid

HRID 5674

반응식

HRID 5674 반응식
[H-].[Na+].[CH2:3]([C:5]1[NH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[C:13](=[O:15])[CH:14]=1)[CH3:4].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([B:24]([OH:26])[OH:25])=[CH:20][CH:19]=1.O>CN(C=O)C>[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([B:24]([OH:26])[OH:25])=[CH:20][CH:19]=2)[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1)[CH3:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27355934-(Bromomethyl)phenylboronic acidHCID 149504752-Ethyl-5,6,7,8-tetrahydroquinolin-4(1H)-one

생성물 1

HCID 151714224-[(2-Ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acid수율 99.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (60% dispersion in oil; 180 mg) was added to a mixture of 2-ethyl-5,6,7,8-tetrahydro-4(1H)-quinolone (660 mg) and 4-bromomethylphenylboronic acid (800 mg) (obtained as described in J. Amer. Chem. Soc. 1958, 80, 835) in DMF (12 ml) under an atmosphere of argon. The mixture was stirred for 40 hours and then water (0.2 ml) was added. Volatile material was removed by evaporation and the residue was dissolved in warm 0.5M sodium hydroxide solution (10 ml). Insoluble material was removed by filtration and the filtrate was acidified to pH 4 with 20% citric acid solution. The precipitate solid was collected by filtration, washed with water (20 ml) and dried under high vacuum to give 4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acid (C) (1.15 g), m.p. 229°-231° C.; NMR (d6 -DMSO): 1.3(t,3H), 1.6-1.9(m,4H), 2.5-2.7(m,2H), 2.75-2.95(m, 4H), 5.4(s,2H), 7.3(d,2H), 7.4(s,1H, 7.5(d,2H).

후처리

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residue was dissolved in warm 0.5M sodium hydroxide solution (10 ml)
  3. customInsoluble material was removed by filtration
  4. filtrationThe precipitate solid was collected by filtration
  5. washwashed with water (20 ml)
  6. customdried under high vacuum

출처 및 근거

ORD 기록
ord-453bbeae00f848f6ad982371dbf56ba9
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245035

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