Sodium Cyanide → HCID 18545965, compound

HRID 2304458Notes

Reaction equation

HRID 2304458 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][OH:12])=[CH:4][CH:3]=1.[C:13]([Cu])#[N:14].[C-]#N.[Na+]>CN1CCCC1=O>[C:13]([C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][OH:12])=[CH:4][CH:3]=1)#[N:14]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 12892145HCID 12892145, compoundHCID 178418546HCID 178418546, compound2×

Product 1

HCID 18545965HCID 18545965, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 6-bromo-1-indanylmethanol (20 g) in N-methyl-2-pyrrolidone (NMP) (380 ml) was added CuCN (79 g). The mixture was heated at 160° C. for 6 hours. After cooling to 80-90° C. the mixture was poured into an aqueous solution (500 ml) of NaCN (4g). After stirring for 20 minutes excess CuCN was filtered off. Ethyl acetate (300 ml) was added and the organic phase was separated and worked-up. The remaining oil was dissolved in diethyl ether (300 ml) and washed with saturated brine (2×100 ml). The organic phase was separated and worked up according to the general procedure leaving 14.6 g of crude title compound 2a as a visceous oil. Column chromatography on silica gel (eluent:ethylacetat/heptane 6:4) afforded pure 2a (8.7 g) which was used without further purification.

Workup

  1. temperatureAfter cooling to 80-90° C. the mixture
  2. filtrationwas filtered off
  3. additionEthyl acetate (300 ml) was added
  4. customthe organic phase was separated
  5. dissolutionThe remaining oil was dissolved in diethyl ether (300 ml)
  6. washwashed with saturated brine (2×100 ml)
  7. customThe organic phase was separated
  8. customleaving 14.6 g of crude title compound 2a as a visceous oil

Sources & evidence

ORD record
ord-e29848a6798c4bb69eb0e98fecec3326
Source dataset
uspto-grants-2002_08
Patent number
US06436940B1

Reaction notes

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