Diethyl Ether → HCID 68328241, 화합물

HRID 2281195노트

반응식

HRID 2281195 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11](C(OCC)=O)[S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:18][Mg]Br.C([O:23][CH2:24][CH3:25])C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([C:24]([OH:23])([CH3:25])[CH3:18])[S:10][N:9]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 68327941HCID 68327941, 화합물HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 68328241HCID 68328241, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred and cooled (0° C.) solution of ethyl 3-(4-fluorophenyl)isothiazole-5-carboxylate (38.50 g, 153.2 mmol) in THF (400 mL) was added a solution of methylmagnesium bromide in diethyl ether (3.0 M, 128 mL, 384 mmol), dropwise over 20 minutes. After another 1.5 hours at 0° C. the reaction was quenched by the slow addition of ethyl acetate (20 mL) and concentrated. The residue was taken up in aqueous NH4Cl (400 mL) and extracted with ethyl acetate (2×150 mL). The combined extracts were dried (Na2SO4) and concentrated. The resulting amber syrup was purified by flash chromatography using a hexane/ethyl acetate gradient to afford 2-(3-(4-fluorophenyl)isothiazol-5-yl)propan-2-ol as soft, golden solid (29.02 g, 80%).

후처리

  1. customAfter another 1.5 hours at 0° C. the reaction was quenched by the slow addition of ethyl acetate (20 mL)
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting amber syrup was purified by flash chromatography

출처 및 근거

ORD 기록
ord-7433c9c60a1b4118abc3576bcaffcdc5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139580B2

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