3,4-dihydro-2H-pyran → 3-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile

HRID 1243503ノート

反応式

HRID 1243503 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

参加物

5

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 27346773-(Hydroxymethyl)benzonitrile

生成物 1

HCID 219279093-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile収率 89.9%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

3-(Hydroxymethyl)benzonitrile (5.00 g; 37.6 mmoles) and 3,4-Dihydro-2H-pyran (3.77 mL; 41.4 mmoles) were dissolved in methylene chloride (25 mL) under nitrogen and the solution was cooled to 5° C. p-Toluenesulfonic acid monohydrate (74 mg; 0.37 mmoles) was added and the mixture was stirred for 2 hours at 25° C. The reaction mixture was diluted with methylene chloride (25 mL). The solution was washed with aqueous sodium bicarbonate solution (30 mL) and aqueous sodium chloride solution (30 mL). The solution was dried over sodium sulfate and filtered. The solvent was removed under vacuum to give the product, 3-[(tetrahydro-2H-pyran-2-yloxy)methyl]benzo-nitrile (7.34 g; 89%) as an oil. 1H NMR (400 MHz) CDCl3 δ 7.68–7.70 (1H, m), 7.54–7.61 (2H, m), 7.42–7.48 (1H, m), 4.82 (1H, d, J=12.5 Hz), 4.72 (1H, t, J=3.3 Hz), 4.53 (1H, d, J=12.5 Hz), 3.84–3.92 (1H, m), 3.53–3.60 (1H, m), 1.60–1.95 (6H, m).

後処理

  1. additionwas added
  2. washThe solution was washed with aqueous sodium bicarbonate solution (30 mL) and aqueous sodium chloride solution (30 mL)
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-8ff52e5946394e41b2ced091c33361c8
出典データセット
uspto-grants-2006_10
特許番号
US07119098B2

反応ノート

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