Propargyl bromide → 4-[(2-Propynyloxy)methyl]benzyl alcohol

HRID 78207

反応式

HRID 78207 の反応式
[H-].[Na+].O1C[CH2:6][CH2:5][CH2:4]1.[C:8]1([CH2:16][OH:17])[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.C(Br)C#C>O.CN(C)C=O>[CH2:6]([O:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:16][OH:17])=[CH:9][CH:10]=1)[C:5]#[CH:4]

参加物

7

反応物 4

HCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 115061,4-BenzenedimethanolHCID 24758Sodium hydride

生成物 1

HCID 545201314-[(2-Propynyloxy)methyl]benzyl alcohol収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of sodium hydride (400 mg, 8.4 mmol, 50% in oil) and tetrahydrofuran (30 mL) was added 1,4-benzenedimethanol (2.3 g, 17 mmol) at 0° C., and then N,N-dimethylformamide (30 mL) was added. The reaction mixture was stirred at room temperature for 10 minutes, after which propargyl bromide (1.0 g, 8.4 mmol) was added dropwise to the reaction mixture at 0° C. The reaction mixture was stirred at room temperature for 1 hour, after which water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed and saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue thus obtained was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:2) to obtain the title compound (860 mg, 58%).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed
  4. concentrationsaturated aqueous sodium chloride, and was concentrated under a reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by NH silica gel column chromatography (heptane:ethyl acetate=3:2)

出典と根拠

ORDレコード
ord-97fe8d2391d4406db3bd358729a1d61d
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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