Water → HCID 22412559, compound

HRID 439661Notes

Reaction equation

HRID 439661 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:6]([CH2:16][OH:17])=[CH:5][C:4]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[C-:25]#[N:26].[Na+].O>CN(C=O)C>[CH2:19]([O:18][C:4]1[CH:5]=[C:6]([CH2:16][OH:17])[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][C:3]=1[CH2:2][C:25]#[N:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 22412551HCID 22412551, compound

Product 1

HCID 22412559HCID 22412559, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the chloride (31) (1.52 g) and sodium cyanide (0.22 g) in DMF (50 ml) was stirred at 60° C. for 3 h. It was poured into water (100ml), and extracted with ether -hexane (1:1, 150 ml ). The organic fraction was washed with water, dried (MgSO4) and the solvent evaporated to give an oil, which was crystallised from hexane (80 ml) to give (32), (1.31 g, 88%), as needles, m.p 63°-66° C., Found C. 73.0, 9.7, N 3.8, C21H33NO3 requires C 72.6, 9.6, N 4.0%!; vmax (KBr)/cm-1 3334 m, 2250 m, 1511 s, 1425 s, 1395 s, 1216 s, 1192 s, 1034 s, 998 s, 871 m, 724 m; δH (250.1 MHZ; CDCl3) 0.9-1.9 (22H, m), 4.36 (4H, m), 2.42 (1H, t, J=5), 3.68 (2H, s), 4.66 (2H, d, J=5), 6.84 (1H, s), 6.89 (1H, s); δC (62.9 MHz; CDCl3) 14.1, 18.7, 22.7, 25.9, 29.4, 31.7, 62.0, 69.1, 112.4, 112.7, 118.3, 130.2, 150.2, 150.7, m/z (CI) 347 (M+, 43), 330 (100), 263 (5).

Workup

  1. extractionextracted with ether -hexane (1:1, 150 ml )
  2. washThe organic fraction was washed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated
  5. customto give an oil, which
  6. customwas crystallised from hexane (80 ml)

Sources & evidence

ORD record
ord-743abc66e2d24cd1b0c59b502adf79bf
Source dataset
uspto-grants-1996_05
Patent number
US05514878

Reaction notes

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