Methanol → HCID 21966474, compound

HRID 2212605Notes

Reaction equation

HRID 2212605 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)=O)C.[H-].CO.O>C1(C)C=CC=CC=1>[F:23][C:20]([F:21])([F:22])[S:17]([O:16][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([CH:4]=[O:3])[CH:15]=1)(=[O:18])=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 166653HydrideHCID 58678620HCID 58678620, compound

Product 1

HCID 21966474HCID 21966474, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-trifluoromethanesulfonyloxy-quinoline-2-carboxylic acid ethyl ester (4.5 g, 12.88 g) in toluene (80 mL) was added slowly under argon at −78° C. diisobuthylaluminum hydride (1.5M in toluene, 12.88 mL, 19.33 mmol). The reaction mixture was stirred at −78° C. for 1 hour. Methanol (13 mL) was added slowly followed by water (26 mL). The reaction mixture was slowly warmed up to room temperature extracted with ethylacetate and washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (5–10% ethylacetate in hexane) to give 2.9 g of 4-trifluoromethanesulfonyloxy-quinoline-2-carbaldehyde (74%). 1H NMR (300 MHz; DMSO-d6): 8–8.2 (m, 4 H), 8.43 (m, 1 H), 10.05 (s, 1H).

Workup

  1. temperatureThe reaction mixture was slowly warmed up to room temperature
  2. extractionextracted with ethylacetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on silica gel (5–10% ethylacetate in hexane)

Sources & evidence

ORD record
ord-90e77e8c58494f0a8c4a742db305fd70
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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