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

HRID 1406053ノート

反応式

HRID 1406053 の反応式
[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

参加物

5

反応物 2

HCID 79895-Hexene-2-oneHCID 178506198HCID 178506198、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c9d03a47f7a94c1b9e9c4369769b597d
出典データセット
uspto-grants-2014_12
特許番号
US08916564B2

反応ノート

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