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

HRID 1701248ノート

反応式

HRID 1701248 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f21dd835ad024c0ca347348c9f23ba6c
出典データセット
uspto-grants-1980_03
特許番号
US04191842

反応ノート

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