Ethylene Glycol → HCID 19600975, compound

HRID 610079Notes

Reaction equation

HRID 610079 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:8](=[O:18])[CH2:7]2)(=[O:3])[CH3:2].[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:2][C:1]1([C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[N:9]([CH2:13][C:14]([F:15])([F:16])[F:17])[C:8](=[O:18])[CH2:7]3)[O:21][CH2:20][CH2:19][O:3]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 19600991HCID 19600991, compound

Product 1

HCID 19600975HCID 19600975, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-acetyl-1-(2,2,2-trifluoro-ethyl)-1,3-dihydro-indol-2-one (1.04 g, 4.0 mmol), ethylene glycol (1.37 mL, 24 mmol) and p-toluenesulfonic acid (10 mg) in benzene (25 mL) was heated to reflux for 4 hours in a flask fitted with a Dean-Stark trap. The solution was diluted with ethyl acetate, washed with saturated sodium bicarbonate, water and brine, dried over magnesium sulfate and concentrated in vacuo to an oil which solidified upon standing (1.19 g, 98%, mp 87-89° C.).

Workup

  1. temperatureto reflux for 4 hours in a flask
  2. customfitted with a Dean-Stark trap
  3. washwashed with saturated sodium bicarbonate, water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to an oil which

Sources & evidence

ORD record
ord-ae4230352a1e4ad38e40a135d620c34e
Source dataset
uspto-grants-1999_12
Patent number
US05998463

Reaction notes

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