Acetone → (4-Ethoxy-3-methanesulfonyl-quinolin-6-yl)-methanol

HRID 1297735Notes

Reaction equation

HRID 1297735 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:9]2[O:20][CH2:21][CH3:22])=O)C.CC(C)=O.C(=O)=O.CC(C[AlH]CC(C)C)C>ClCCl.C1(C)C=CC=CC=1.CO>[CH2:21]([O:20][C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH2:4][OH:3])[CH:7]=2)[N:12]=[CH:11][C:10]=1[S:16]([CH3:19])(=[O:18])=[O:17])[CH3:22]

Participants

8

Reactant 4

HCID 180AcetoneHCID 280Carbon DioxideHCID 14487Diisobutylaluminum hydrideHCID 58585859HCID 58585859, compound

Product 1

HCID 58585781(4-Ethoxy-3-methanesulfonyl-quinolin-6-yl)-methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-ethoxy-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester (example 74a) in anhydrous dichloromethane (500 mL) was cooled to −78 degrees by acetone and dry-ice bath. DIBAL-H in toluene (1M, 50.8 mL, 50.8 m mol) was added dropwise into the above solution. The solution was allowed to react at −78 degrees for 4 hours. Then methanol was added to the reaction mixture. The resulted reaction mixture was stirred at −78 degrees for another 30 min, and then warmed to room temperature slowly. After the reaction, the solvent was evaporated; dichloromethane was added to the residue. After filtering out the insoluble, filtrate was collected, and concentrated to give (4-ethoxy-3-methanesulfonyl-quinolin-6-yl)-methanol which was used in the next step reaction without further purification. LC-MS m/e 282 (MH+).

Workup

  1. customto react at −78 degrees for 4 hours
  2. customThe resulted reaction mixture
  3. customAfter the reaction
  4. customthe solvent was evaporated
  5. additiondichloromethane was added to the residue
  6. filtrationAfter filtering out the insoluble, filtrate
  7. customwas collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-76cab3e0a64b4b019a32efbd82f29805
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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