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

HRID 26786노트

반응식

HRID 26786 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+].CO>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

5

반응물 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 86735108bromo ether (S)-(+)-3-tert. butoxy-2-methyl-1-bromopropane

생성물 1

HCID 12923321(R)-(+)-4-tert. butoxy-3-methylbutyronitrile수율 64.6%

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 methanol and 36 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 (11.03 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-012c4d5ae5ea445d8b3030b7309cc627
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04151205

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