Sodium Cyanide → (R)-(+)-4-tert. butoxy-3-methylbutyronitrile

HRID 2072351노트

반응식

HRID 2072351 반응식
[C:1]([O:5][CH2:6][C@H:7]([CH3:10])[CH2:8]Br)([CH3:4])([CH3:3])[CH3:2].BrOBr.[C-:14]#[N:15].[Na+]>O>[C:1]([O:5][CH2:6][C@H:7]([CH3:10])[CH2:8][C:14]#[N:15])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 86735108bromo ether (S)-(+)-3-tert. butoxy-2-methyl-1-bromopropane

생성물 1

HCID 12923321(R)-(+)-4-tert. butoxy-3-methylbutyronitrile수율 66.2%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A mixture of 23.1 g. (0.11 mole) of bromo ether (S)-(+)-3-tert. butoxy-2-methyl-1-bromopropane and 11.07 g. (0.225 mole) of sodium cyanide in 144 ml. of water was stirred and refluxed for 17 hours. After cooling, the reaction mixture was diluted with water and worked up by extraction with CH2Cl2 in the manner of Example 1. The crude product was chromatographed on 500 g. of silica gel. Elution with 9:1 parts by volume and 4:1 parts by volume hexane-ether followed by evaporative distillation gave (R)-(+)-4-tert. butoxy-3-methylbutyronitrile (11.3 g.; 64.5%) as a colorless liquid, b.p. 88°-90° C. (bath temperature) (11 mm Hg.); [α]25D + 7.41° (c 1.8, C6H6).

후처리

  1. additionA mixture of 23.1 g
  2. temperaturerefluxed for 17 hours
  3. temperatureAfter cooling
  4. extractionworked up by extraction with CH2Cl2 in the manner of Example 1
  5. customThe crude product was chromatographed on 500 g
  6. washElution with 9:1 parts by volume and 4:1 parts by volume hexane-ether
  7. distillationfollowed by evaporative distillation

출처 및 근거

ORD 기록
ord-8ab9029872194038910eb0ca0ca349b6
출처 데이터셋
uspto-grants-1977_09
특허 번호
US04051153

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