Acetone Cyanohydrin → HCID 59783608, compound

HRID 718055Notes

Reaction equation

HRID 718055 reaction equation
[CH:1]1[C:6]2[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][C:17]=3[F:24])=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C-]#N.[K+].[OH:35][C:36](C)(C)C#N>CO>[CH:1]1[C:6]2[C:7]([C:16]3[CH:23]=[CH:22][C:19]([C:20]([O:35][CH3:36])=[O:21])=[CH:18][C:17]=3[F:24])=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 59783559HCID 59783559, compound

Product 1

HCID 59783608HCID 59783608, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of compound 102 (0.59 g, 1.90 mmol), triethylamine (1.6 mL, 11.48 mmol), potassium cyanide (0.061 g, 0.93) and 2-hydroxy-2-methylpropanenitrile (1 mL, 10.93) in methanol (15 mL) was stirred at 40° C. for 24 h then solvent evaporated. The resulting crude residue was purified on ISCO (0-100% EtOAc in Hexanes) to afford title compound 103 (0.364 g, 56%) as a yellow solid. LRMS (ESI): (calc) 347.10. (found) 348.4 (MH)+.

Workup

  1. customsolvent evaporated
  2. customThe resulting crude residue was purified on ISCO (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-05ff5c1f66ab40be8371d9063d06df49
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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