Triethylamine → HCID 21948828, compound

HRID 2182746Notes

Reaction equation

HRID 2182746 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([C:8]([CH3:20])([CH3:19])[CH2:9][C:10]([C:15]([F:18])([F:17])[F:16])([OH:14])[CH:11]([OH:13])[CH3:12])[CH:7]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CS(C)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([C:8]([CH3:19])([CH3:20])[CH2:9][C:10]([OH:14])([C:15]([F:18])([F:17])[F:16])[C:11](=[O:13])[CH3:12])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 219488565-(5-Fluoro-2-methoxyphenyl)-5-methyl-3-(trifluoromethyl)hexane-2,3-diol

Product 1

HCID 21948828HCID 21948828, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

1.46 g (4.5 mmol) of 5-(5-fluoro-2-methoxyphenyl)-5-methyl-3-(trifluoromethyl)hexane-2,3-diol and 3.14 ml (22.5 mmol) of triethylamine in 16.3 ml of DMSO and 50 ml of methylene chloride are mixed in portions with 4.3 g (27 mmol) of pyridine-sulfur trioxide complex at room temperature. After 20 hours at room temperature, it is hydrolyzed with saturated ammonium chloride solution while being cooled with ice and extracted with diethyl ether. The combined extracts are dried (sodium sulfate) and concentrated by evaporation. Column chromatography on silica gel with hexane-ethyl acetate yields 1.04 g of the product.

Workup

  1. temperaturewhile being cooled with ice
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined extracts are dried (sodium sulfate)
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-03f51f42d9e14789992ee75b2ae312f7
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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