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Acetone → 4-(2-Cyclopenten-1-yl)-2-methyl-2-butanol

HRID 2085011
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반응식

HRID 2085011 반응식
Cl[CH2:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]=[CH:5]1.[Mg].Cl.[CH3:11][C:12]([CH3:14])=[O:13]>C1COCC1>[CH:4]1([CH2:3][CH2:2][C:12]([CH3:14])([OH:13])[CH3:11])[CH2:8][CH2:7][CH:6]=[CH:5]1
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참가 물질

6

반응물 4

HCID 180Acetone2회HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 13405540HCID 13405540, 화합물

생성물 1

HCID 227288324-(2-Cyclopenten-1-yl)-2-methyl-2-butanol수율 47%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

5.3 g (40.6 mmol) of 3-(2-chloroethyl)-1-cyclopentene (obtained according to Hill et al. in J. Org. Chem., 1969, 3681), dissolved into 30 ml of dry THF, were added dropwise into a three necks 200 ml flask containing 1.2 g (48.7 mmol) of magnesium and 5 ml of dry THF. After a 2 hours stirring at room temperature, 2.8 g (48.7 mmol) of acetone were slowly added to the reaction mixture. 15 Minutes after the addition of the acetone, the reaction mixture was slowly hydrolysed using 1 M aqueous HCl, and extracted with ether. Then, the organic phase was washed twice with water and twice with brine, dried over MgSO4 and concentrated. The crude product was purified by chromatography over silica (eluant: cyclohexane/ethyle acetate=9/1). It was thus obtained 2.7 g of the title compound (yield=47%).

후처리

  1. additionwere added dropwise into a three necks 200 ml flask
  2. extractionextracted with ether
  3. washThen, the organic phase was washed twice with water and twice with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography over silica (eluant: cyclohexane/ethyle acetate=9/1)

출처 및 근거

ORD 기록
ord-2f176271d4b2461bac1f24d269c2f694
출처 데이터셋
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06720295B2

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