Ethanol → HCID 15617943, compound

HRID 703920Notes

Reaction equation

HRID 703920 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[O:14][Si](C(C)(C)C)(C)C)[CH:2]=[CH2:3].[C-:22]#[N:23].[K+].C(O)C>O>[OH:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:1][CH2:2][CH2:3][C:22]#[N:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 15617924HCID 15617924, compound

Product 1

HCID 15617943HCID 15617943, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of the product of Example 122 Part C (3.79 g, 0.010 mole), potassium cyanide (0.72 g, 0.011 mole), ethanol (15 mL) and water (2 mL) was heated at reflux for 20 hours. The cooled mixture was poured into water and extracted with ethyl acetate. The crude product was chromatographed with 1:1 ether/hexane and recrystallized (cyclohexane/toluene) to provide the title compound (0.73 g, 35%) as a white solid, mp 76°-78°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. extractionextracted with ethyl acetate
  4. customThe crude product was chromatographed with 1:1 ether/hexane
  5. customrecrystallized (cyclohexane/toluene)

Sources & evidence

ORD record
ord-fccf5b14a1044fa3bf50ed684eff8b47
Source dataset
uspto-grants-1991_01
Patent number
US04985435

Reaction notes

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