Ethylene Glycol → HCID 66661680, compound

HRID 557865Notes

Reaction equation

HRID 557865 reaction equation
[CH:1]1([CH:6]([F:18])[C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]#N)[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:19].[Na+].C(O)C[OH:23]>O>[CH:1]1([CH:6]([F:18])[C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]([OH:23])=[O:19])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 66662149HCID 66662149, compound

Product 1

HCID 66661680HCID 66661680, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

To a mixture of 1-{4-[cyclopentyl(fluoro)methyl]phenyl}cyclopropanecarbonitrile (600.0 mg, 0.002466 mol) and 19.4 M of sodium hydroxide in water (0.51 mL) was added 1,2-ethanediol (5 mL, 0.09 mol), and the mixture was refluxed at 100° C. overnight. After cooling down to rt, the reaction mixture was poured into water and extracted with ether. The aqueous phase then was acidified with HCl and extract with ether. Then the organic phase was washed with brine, dryed over MgSO4, and concentrated to afford the desired product.

Workup

  1. temperatureAfter cooling down to rt
  2. extractionextracted with ether
  3. extractionextract with ether
  4. washThen the organic phase was washed with brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ec8922dcb104d62ad6432618c4412df
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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