2,2-Dimethoxypropane → 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroquinolin-5(6H)-one

HRID 1506411Notes

Reaction equation

HRID 1506411 reaction equation
[OH:1][CH:2]([C:5]1[CH:14]=[CH:13][C:12]2[C:11](=[O:15])[CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1)[CH2:3][OH:4].CO[C:18](OC)([CH3:20])[CH3:19].[C@@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CC(C)=O>[CH3:19][C:18]1([CH3:20])[O:1][CH:2]([C:5]2[CH:14]=[CH:13][C:12]3[C:11](=[O:15])[CH2:10][CH2:9][CH2:8][C:7]=3[N:6]=2)[CH2:3][O:4]1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 131278(R)-camphorsulfonic acidHCID 671713442-(1,2-dihydroxyethyl)-7,8-dihydroquinolin-5(6H)-one

Product 1

HCID 671722122-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroquinolin-5(6H)-oneYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(1,2-dihydroxyethyl)-7,8-dihydroquinolin-5(6H)-one (Preparation 54D, 0.226 g, 1.09 mmol), 2,2-dimethoxypropane (0.402 mL, 3.27 mmol), and (1R)-(−)-camphorsulfonic acid (0.051 g, 0.22 mmol) in acetone (6 mL) was stirred at room temperature overnight. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and concentrated under reduced pressure. The aqueous residue was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer was collected, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated and purified by flash silica gel chromatography using a mixture of ethyl acetate in hexane (50%) to afford 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroquinolin-5(6H)-one (0.182 g, 0.736 mmol, 68% yield) as a clear, colorless oil. The product had an HPLC ret. time=1.75 min. (condition A); LC/MS M+1=247.9.

Workup

  1. customThe reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate
  2. concentrationconcentrated under reduced pressure
  3. additionThe aqueous residue was diluted with ethyl acetate
  4. washwashed with a saturated aqueous solution of sodium bicarbonate and brine
  5. customThe organic layer was collected
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by flash silica gel chromatography
  10. additiona mixture of ethyl acetate in hexane (50%)

Sources & evidence

ORD record
ord-6faff6b81dac4972ac30fe07b60979ed
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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