Water → 2-(2,4-Dichlorophenyl)-1-(2-chlorothiazol-5-yl)propan-2-ol

HRID 345430

반응식

HRID 345430 반응식
C([Li])CCC.[Cl:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH3:23])[CH2:22][O:21]1.O>CCCCCC.O1CCCC1>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]([OH:21])([CH3:22])[CH2:23][C:9]1[S:8][C:7]([Cl:6])=[N:11][CH:10]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 764292-ChlorothiazoleHCID 199924372-(2,4-Dichlorophenyl)-2-methyloxiraneHCID 178418339Butyllithium

생성물 1

HCID 199924352-(2,4-Dichlorophenyl)-1-(2-chlorothiazol-5-yl)propan-2-ol수율 76.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

Butyl lithium (2.5 M, 12.5 ml) in hexane was added to a solution of 2-chlorothiazole (3.6 g, 30 mmol) in tetrahydrofuran (100 ml) at -78° C. under an atmosphere of nitrogen. After 10 minutes, a solution of 2-(2,4-dichlorophenyl)-2-methyloxirane (5.4 g, 26 mmol) in tetrahydrofuran (40 ml) was added and the mixture was slowly allowed to warm to room temperature and then stirred for a further 3 hours. Water was added and the tetrahydrofuran was then evaporated under reduced pressure. The residue was extracted with ethyl acetate (2×300 ml) and the combined organic extract was washed with saturated sodium chloride solution and then dried. Flash chromatography of the residue on a silica gel column using ethyl acetate-petroleum ether as eluant gave 2-(2,4-dichlorophenyl)-1-(2-chlorothiazol-5-yl)-propan-2-ol (6.4 g) as a white solid, m.pt. 164° C.

후처리

  1. customthe tetrahydrofuran was then evaporated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate (2×300 ml)
  3. extractionthe combined organic extract
  4. washwas washed with saturated sodium chloride solution
  5. customdried

출처 및 근거

ORD 기록
ord-e746db297e514636ba9f3b517d4c3955
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057529

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