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

HRID 654367

反応式

HRID 654367 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8198be65b7114fb4989e5a1ca9a5300a
出典データセット
uspto-grants-1992_07
特許番号
US05130318

関連ノート

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