Isopropanol → 1-(2-Chloro-cyclohex-1-enyl)-ethanol

HRID 2391082ノート

反応式

HRID 2391082 の反応式
[Cl:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[CH:8]=[O:9].[CH3:10][Mg]Br.CC(O)C>C1COCC1>[Cl:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[CH:8]([OH:9])[CH3:10]

参加物

5

反応物 3

HCID 3776IsopropanolHCID 118048922-Chlorocyclohex-1-enecarbaldehydeHCID 178418573HCID 178418573、化合物

生成物 1

HCID 137855171-(2-Chloro-cyclohex-1-enyl)-ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-chloro-cyclohex-1-enecarbaldehyde (13.6 mmol) in THF at 0° C. was added methyl magnesium bromide (3M in THF; 5.4 mL, 16.32 mmol). The reaction was stirred under N2 for 1 hour, and then iPrOH (2 mL) was added. The mixture was concentrated, and the residue was diluted with 1N aqueous HCl and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NH4Cl, dried over MgSO4, filtered, and concentrated, and the crude material was purified by silica gel chromatography to give the title compound.

後処理

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with 1N aqueous HCl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with saturated aqueous NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-c1de9bb69f974f1984bdc55d78bb03eb
出典データセット
uspto-grants-2012_09
特許番号
US08273780B2

反応ノート

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