Sodium Cyanide → HCID 19364626, compound

HRID 1489494Notes

Reaction equation

HRID 1489494 reaction equation
[C-:1]#[N:2].[Na+].[Si:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]>CS(C)=O>[Si:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:1]#[N:2])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 8929Sodium Cyanide2×HCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilane

Product 1

HCID 19364626HCID 19364626, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Sodium cyanide (1.2 g) dissolved in dimethylsulphoxide was heated at 90° C. for 30 min. Solid 1-t-butyldimethylsilyloxy-6-bromohexane (5.8 g, compound X1) prepared according to the method previously described (ref. 37), then was added into the sodium cyanide solution. After heating at 120°-130 C. for 20-180 min, the reaction mixture was poured into ice-cold water and the aqueous layer was extracted with ether, washed with brine, dried and concentrated. The product was distilled at 0.5 Torr and 107° C. to give a colourless oil. High resolution mass spectrometer for C12 H24 O N Si: calculated 226.1627, found 226.1624.

Workup

  1. temperatureAfter heating at 120°-130 C
  2. additionthe reaction mixture was poured into ice-cold water
  3. extractionthe aqueous layer was extracted with ether
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. distillationThe product was distilled at 0.5 Torr and 107° C.
  8. customto give a colourless oil

Sources & evidence

ORD record
ord-17e560e1eba845c1aca24bf4eb3a8464
Source dataset
uspto-grants-1997_10
Patent number
US05679352

Reaction notes

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