Ethanol → (R)-(+)-4-tert. Butoxy-2-methylbutyronitrile

HRID 26788Notes

Reaction equation

HRID 26788 reaction equation
C1(C)C=CC(S(OC[C@@H:12]([CH3:19])[CH2:13][O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=O)=O)=CC=1.[C-:21]#[N:22].[Na+].[CH2:24](O)C>O>[C:15]([O:14][CH2:13][CH2:12][C@@H:19]([CH3:24])[C:21]#[N:22])([CH3:16])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 86735106(S)-(+)-3-tert. butoxy-2-methyl-1-propyl p-toluenesulfonate

Product 1

HCID 86735109(R)-(+)-4-tert. Butoxy-2-methylbutyronitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.4 g. (0.021 mole) of (S)-(+)-3-tert. butoxy-2-methyl-1-propyl p-toluenesulfonate and 2.09 g. (0.043 mole) of sodium cyanide in 63 ml. of ethanol and 7 ml. of water was stirred and refluxed for 11 hours. After cooling, the reaction mixture was diluted with ice-water and worked up by extraction with CH2Cl2 in the manner of Example 1. The crude product (3.7 g.) was chromatographed on 125 g. of silica gel. Elution with 4:1 parts by volume hexane-ether gave 2.98 g. (91.7%) of R-(+)-4-tert. butoxy-3-methylbutyronitrile as a colorless liquid.

Workup

  1. additionA mixture of 6.4 g
  2. temperaturerefluxed for 11 hours
  3. temperatureAfter cooling
  4. extractionworked up by extraction with CH2Cl2 in the manner of Example 1
  5. customThe crude product (3.7 g.) was chromatographed on 125 g
  6. washElution with 4:1 parts by volume hexane-ether
  7. customgave 2.98 g

Sources & evidence

ORD record
ord-c36fc3ba4fce4ba19e75adfd7fb08883
Source dataset
uspto-grants-1979_04
Patent number
US04151205

Reaction notes

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