N,N-dimethylformamide;hydrochloride → 4-Chloro-2-fluoro-5,5-dimethoxy-4-methylpentanenitrile

HRID 638513

반응식

HRID 638513 반응식
Cl[C:2]([F:14])([CH2:5][C:6]([Cl:13])([CH3:12])[CH:7]([O:10][CH3:11])[O:8][CH3:9])[C:3]#[N:4].Cl.CN(C)C=O>[Hg].C(#N)C.[Cd]>[Cl:13][C:6]([CH3:12])([CH:7]([O:8][CH3:9])[O:10][CH3:11])[CH2:5][CH:2]([F:14])[C:3]#[N:4]

참가 물질

6

반응물 2

HCID 10920465N,N-dimethylformamide;hydrochlorideHCID 135375282,4-Dichloro-2-fluoro-5,5-dimethoxy-4-methylpentanenitrile

생성물 1

HCID 135375294-Chloro-2-fluoro-5,5-dimethoxy-4-methylpentanenitrile수율 357.7%

시약·촉매·용매 3

HCID 23973Cadmium촉매HCID 6342Acetonitrile용매2회HCID 23931Mercury용매

실험 절차

A reaction mixture containing 5 g (0.045 mole) of cadmium metal dissolved in 100 g of mercury and 100 ml of acetonitrile was brought to reflux and 10.8 g (0.04 mole) of 2,4-dichloro-2-fluoro-5,5-dimethoxy-4-methylpentanenitrile and 0.05 mole of dimethylformamidehydrochloride in 50 ml of acetonitrile were added dropwise. After the addition was complete refluxing was maintained for an additional 5 hours. The salts and Hg were removed by filtration and the solvent was removed in vacuo. The residue was distilled through a Kuglerohr apparatus to afford 30 g of crude 4-chloro-2-fluoro-5,5-dimethoxy-4-methylpentanenitrile which was distilled through a spinning band column. Fractions boiling between 52°-55° C., 0.3 mm Hg, were collected and were shown to be essentially pure diasteromeric 4 -chloro-2-fluoro-5,5-dimethoxy-4-methylpentanenitriles, 'Hnmr (Acetone d6TMS) δ 1.5-1.75 (m, 3H, --CH3); δ 2.60 (dm, 2H, -- CH2 --), JHF 20.76 z; δ 3.58 ##STR7## δ 5.8 (dt, 1H, --CHF--); JH2F 46.6 Hz. IR NaCl neat 2260 cm-1 ; 1070 cm-1.

후처리

  1. temperatureto reflux
  2. additionAfter the addition
  3. temperaturewas complete refluxing
  4. temperaturewas maintained for an additional 5 hours
  5. customThe salts and Hg were removed by filtration
  6. customthe solvent was removed in vacuo
  7. distillationThe residue was distilled through a Kuglerohr apparatus

출처 및 근거

ORD 기록
ord-bcced2175801459997d9ab81e6f93bb7
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04562009

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