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

HRID 557657노트

반응식

HRID 557657 반응식
[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]

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 118048922-Chlorocyclohex-1-enecarbaldehydeHCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d153e7ecfc4d40fc9f04dfff3e5b9ba4
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058300B2

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