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

HRID 1905538노트

반응식

HRID 1905538 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 200639705-(5-Chloropentyl)-3-methylisothiazole수율 49.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-283b3786587448519ce22cc343d4e025
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04843087

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