Sodium Cyanide → Benzyl 10-cyano-2-cyclopentyldecanoate

HRID 977644Notes

Reaction equation

HRID 977644 reaction equation
[CH:1]1([CH:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]I)[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C-:26]#[N:27].[Na+]>CS(C)=O>[C:26]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])#[N:27]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 10479189Benzyl 2-cyclopentyl-10-iododecanoate

Product 1

HCID 10473415Benzyl 10-cyano-2-cyclopentyldecanoateYield 93.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of the iodoester from step 2, (3.99 g, 8.7 mmol) and sodium cyanide (0.47 g, 9.6 mmol) in 15 mL of anhyd. DMSO was heated at 70°-75° C. for 30 min. After cooling, the reaction mixture was poured over ice (~ 40 g), extracted into ether and washed successively with water and saturated brine. The organic layer was concentrated to yield an oil (2.89 g). 1H NMR (300 MHz, CDCl3). δ: 7.35 (m, 5H), 5.15 (s, 2H), 2.30(t, 8 Hz, 2H), 2.20(m, 1H), 2.00(m, 1H), 1.3-1.8 (m, 22H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted into ether
  3. washwashed successively with water and saturated brine
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-768acbb8faef44b29df28ee85cc9c518
Source dataset
uspto-grants-1997_03
Patent number
US05614649

Reaction notes

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