2,2,2-Trifluoroethanol → HCID 14622036, compound

HRID 1074288Notes

Reaction equation

HRID 1074288 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11](Cl)=[O:12])=[CH:6][C:5]=1[F:18])[CH3:2].[F:19][C:20]([F:24])([F:23])[CH2:21][OH:22]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([O:22][CH2:21][C:20]([F:24])([F:23])[F:19])=[O:12])=[CH:6][C:5]=1[F:18])[CH3:2]

Participants

5

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 14622035HCID 14622035, compound

Product 1

HCID 14622036HCID 14622036, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

3.0 g (0.011 mol) 2-(4-Ethoxy-3-fluorophenyl)-3,3-dimethylbutyryl chloride was added dropwise to a solution of 1.12 g (0.0121 mol) 2,2,2-trifluoroethanol and 100 mg 4-dimethylaminopyridine in 15 ml pyridine at 0° C. After stirring for two hours at room temperature, tlc showed complete reaction. The mixture was added to ice/water, made weakly acidic, extracted with ether, the extract dried over magnesium sulphate and evaporated under reduced pressure. After silica gel chromatography, 2.80 g (=75.6% of theory) of a pale yellow oil was obtained. nD20 : 1.4783

Workup

  1. customreaction
  2. extractionextracted with ether
  3. dry with materialthe extract dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customAfter silica gel chromatography, 2.80 g (=75.6% of theory) of a pale yellow oil was obtained

Sources & evidence

ORD record
ord-26277bfd5dd1474595e91117cb3d99f1
Source dataset
uspto-grants-1990_11
Patent number
US04973735

Reaction notes

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