Diethyl Ether → HCID 68328241、化合物

HRID 2281195ノート

反応式

HRID 2281195 の反応式
[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

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 68327941HCID 68327941、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 68328241HCID 68328241、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7433c9c60a1b4118abc3576bcaffcdc5
出典データセット
uspto-grants-2015_09
特許番号
US09139580B2

反応ノート

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