Benzyl Bromide → 2-(2-Naphthalenyl)-3-phenylpropionitrile

HRID 330263

反応式

HRID 330263 の反応式
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][C:14]#[N:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>COCCOC>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH:13]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]#[N:15]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 820082-Naphthylacetonitrile

生成物 1

HCID 149606362-(2-Naphthalenyl)-3-phenylpropionitrile収率 40%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

To a refluxing solution of NaH (3.00 g, 75 mmol, 60% dispersion) in DME (150 mL) was added a solution of 2-naphthaleneacetonitrile (12.5 g, 75 mmol) and benzyl bromide (12.8 g, 75 mmol) in DME (75 mL) dropwise over 50 minutes. The resulting solution was kept at reflux for 3 hours and then cooled to room temperature. The volatiles were removed in vacuo and the residue was partitioned between Et2O (100 mL) and H2O (100 mL). The aqueous phase was washed with Et2O (1×150 mL), the organics were dried (MgSO4) and concentrated in vacuo. This residue was purified by preparative HPLC (SiO2 : gradient hexane/EtOAc) to give the title compound as a white solid (7.71 g, 40%).

後処理

  1. temperatureat reflux for 3 hours
  2. customThe volatiles were removed in vacuo
  3. customthe residue was partitioned between Et2O (100 mL) and H2O (100 mL)
  4. washThe aqueous phase was washed with Et2O (1×150 mL)
  5. dry with materialthe organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThis residue was purified by preparative HPLC (SiO2 : gradient hexane/EtOAc)

出典と根拠

ORDレコード
ord-d15056049a82458a98917c13f3a87301
出典データセット
uspto-grants-1990_01
特許番号
US04895861

関連ノート

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