Sodium hydride → 5-(Cyclopropylmethoxy)cyclohex-1-enecarbonitrile

HRID 1852485ノート

反応式

HRID 1852485 の反応式
[OH:1][CH:2]1[CH2:7][C:6]([C:8]#[N:9])=[CH:5][CH2:4][CH2:3]1.[H-].[Na+].Br[CH2:13][CH:14]1[CH2:16][CH2:15]1>CN(C)C=O.CCOC(C)=O>[CH:14]1([CH2:13][O:1][CH:2]2[CH2:7][C:6]([C:8]#[N:9])=[CH:5][CH2:4][CH2:3]2)[CH2:16][CH2:15]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 601605645-Hydroxycyclohex-1-ene-1-carbonitrile2 回

生成物 1

HCID 867310195-(Cyclopropylmethoxy)cyclohex-1-enecarbonitrile

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

To the solution of (R or S)-5-Hydroxycyclohex-1-enecarbonitrile (Intermediate #40, 2.0 g, 16 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (850 mg, 21 mmol, 60% dispersion in oil) at 0° C. The resulting suspension was stirred at ambient temperature for 30 minutes before the addition of bromomethylcyclopropane (3.3 g, 24 mmol). The mixture was then stirred at 75° C. for 6 hours, and diluted with EtOAc (50 mL). The organic solution was washed with brine (2×10 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 2-5% EtOAc/hexane) to afford the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 6.63-6.62 (m, 1H), 3.69-3.66 (m, 1H), 3.34-3.32 (m, 2H), 2.54-2.49 (m, 1H), 2.38-2.30 (m, 1H), 2.29-2.24 (m, 2H), 1.85-1.83 (m, 1H), 1.75-1.72 (m, 1H), 1.08-1.04 (m, 1H), 0.59-0.54 (m, 2H), 0.24-0.20 (1,2H).

後処理

  1. washThe organic solution was washed with brine (2×10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by MPLC on Silica gel (eluting with 2-5% EtOAc/hexane)

出典と根拠

ORDレコード
ord-07a325c52aaf42c3b6850d2f7803de99
出典データセット
uspto-grants-2015_02
特許番号
US08962608B2

反応ノート

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