5-Hexene-2-one → 2-[4-(Trifluoromethyl)phenyl]hex-5-en-2-ol

HRID 1406053노트

반응식

HRID 1406053 반응식
[CH3:1][C:2](=[O:7])[CH2:3][CH2:4][CH:5]=[CH2:6].[F:8][C:9]([F:19])([F:18])[C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1>O1CCCC1.C(OCC)(=O)C>[F:8][C:9]([F:19])([F:18])[C:10]1[CH:15]=[CH:14][C:13]([C:2]([OH:7])([CH2:3][CH2:4][CH:5]=[CH2:6])[CH3:1])=[CH:12][CH:11]=1

참가 물질

5

반응물 2

HCID 79895-Hexene-2-oneHCID 178506198HCID 178506198, 화합물

생성물 1

HCID 867137192-[4-(Trifluoromethyl)phenyl]hex-5-en-2-ol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

A solution of hex-5-en-2-one (1.00 g, 10.2 mmol) in tetrahydrofuran (3 mL) was added to [4-(trifluoromethyl)phenyl]magnesium bromide (0.26 M solution in tetrahydrofuran, 50 mL, 13 mmol) at 0° C. After 15 minutes at 0° C., the reaction mixture was heated at 70° C. for 18 hours, then cooled to room temperature, diluted with ethyl acetate, and washed with saturated aqueous ammonium chloride solution, with water, and with saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 10% to 30% ethyl acetate in heptane) afforded the product as a dark gold oil. Yield: 1.86 g, 7.61 mmol, 75%. 1H NMR of crude product (400 MHz, CDCl3), characteristic peaks: δ 7.59 (br AB quartet, JAB=8 Hz, ΔνAB=19 Hz, 4H), 5.74-5.85 (m, 1H), 4.93-5.01 (m, 2H), 1.59 (s, 3H).

후처리

  1. temperaturecooled to room temperature
  2. washwashed with saturated aqueous ammonium chloride solution, with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (Gradient: 10% to 30% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-c9d03a47f7a94c1b9e9c4369769b597d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916564B2

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