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

HRID 330263

반응식

HRID 330263 반응식
[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]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 820082-Naphthylacetonitrile

생성물 1

HCID 149606362-(2-Naphthalenyl)-3-phenylpropionitrile수율 40%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-d15056049a82458a98917c13f3a87301
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895861

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