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

HRID 1506411노트

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HRID 1506411 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-6faff6b81dac4972ac30fe07b60979ed
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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