3-Methylisothiazole → 5-(5-Chloropentyl)-3-methylisothiazole

HRID 1905538ノート

反応式

HRID 1905538 の反応式
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][N:3]=1.C([Li])CCC.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Cl:18]>O1CCCC1.CCOCC>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:5]1[S:4][N:3]=[C:2]([CH3:1])[CH:6]=1

参加物

6

反応物 3

HCID 127473-MethylisothiazoleHCID 960701-Bromo-5-chloropentaneHCID 178418339Butyllithium

生成物 1

HCID 200639705-(5-Chloropentyl)-3-methylisothiazole収率 49.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6.4 g 3-methylisothiazole in 100 ml dry tetrahydrofuran at -78° C. under nitrogen was slowly added 7.6 ml n-butyllithium (9.5 m). After 15 min. at -78° C., a solution of 12.0 g 1-bromo-5-chloropentane in 10 ml dry ether was added. The reaction mixture was allowed to reach room temperature where it was stirred for 90 min., then diluted with ether, washed with water and sodium chloride solution, and dried over sodium sulfate. Concentration and flash filtration (silica gel, 4:1 hexane/ethyl acetate) gave 6.5 g of 5-(5-chloropentyl)-3-methylisothiazole as a red oil, sufficiently pure (NMR) for use in the subsequent reaction.

後処理

  1. customat -78° C.
  2. customto reach room temperature
  3. washwashed with water and sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and flash filtration (silica gel, 4:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-283b3786587448519ce22cc343d4e025
出典データセット
uspto-grants-1989_06
特許番号
US04843087

反応ノート

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