Ethylene Glycol → HCID 68313710, compound

HRID 626492Notes

Reaction equation

HRID 626492 reaction equation
C(O)CO.[C:5]([CH:7]([C:12]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:21][C:16]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1)C(OC)=O)#[N:6].[OH-].[K+]>O>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:12]1([CH2:7][C:5]#[N:6])[CH2:21][C:16]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 68313977HCID 68313977, compound

Product 1

HCID 68313710HCID 68313710, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Ethylene glycol (300 ml) was added to methyl 2-cyano-2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetate (15.43 g, 49 mmol) followed by potassium hydroxide (5.5 g, 98 mmol), the resulting mix was heated to 120° C., after 3 h, the reaction mix was cooled and water (300 ml) was added, the product was extracted by Et2O (3×400 ml), washed with water (200 ml), dried (Na2SO4) and concentrated, the residual was purified by flash chromatography (340 g silica gel column, eluted by EtOAc in hexane: 3% 2CV; 3-25%, 12 CV; 25-40% 6CV to give 2-[9-(Pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (10.37 g, 82% yield, m/z 257.0 [M+H]+ observed).

Workup

  1. additionthe resulting mix
  2. additionthe reaction mix
  3. temperaturewas cooled
  4. extractionthe product was extracted by Et2O (3×400 ml)
  5. washwashed with water (200 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customthe residual was purified by flash chromatography (340 g silica gel column
  9. washeluted by EtOAc in hexane

Sources & evidence

ORD record
ord-4a28045b6e054db996ddb126e8ca3412
Source dataset
uspto-grants-2016_04
Patent number
US09309234B2

Reaction notes

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