Hydrochloric Acid → 8-(1,3-Dimethoxypropan-2-yloxy)-2-methylquinoline

HRID 339056

반응식

HRID 339056 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:32][O:33][CH2:34][CH:35](O)[CH2:36][O:37][CH3:38].CC(OC(/N=N/C(OC(C)C)=O)=O)C.Cl>C1COCC1.C(OCC)(=O)C.O>[CH3:32][O:33][CH2:34][CH:35]([O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)[CH2:36][O:37][CH3:38]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 121901,3-Dimethoxy-2-propanolHCID 132242-Methyl-8-hydroxyquinolineHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 709841378-(1,3-Dimethoxypropan-2-yloxy)-2-methylquinoline수율 89.15%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-methylquinolin-8-ol (4.10 g, 25.76 mmol), PPh3 (16.89 g, 64.39 mmol) and 1,3-dimethoxypropan-2-ol (4.02 g, 33.48 mmol) in THF (20 mL) was added DIAD (8.40 mL, 41.21 mmol) dropwise at ambient temperature. The reaction mixture was stirred at room temperature for two days. 4 N HCl (7.73 mL, 30.91 mmol in water), water (20 mL), and ethyl acetate (50 mL) were added. The aqueous layer was separated and washed with ethyl acetate. The aqueous layer was neutralized with ammonium hydroxide to about pH 9 and extracted with ethyl acetate (50 mL). The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:2 hexane/ethyl acetate) to give 8-(1,3-dimethoxypropan-2-yloxy)-2-methylquinoline (6.00 g, 89.15%) as an oil.

후처리

  1. customThe aqueous layer was separated
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate (50 mL)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (1:2 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-d2d57cd034be462d8e17eb4ed307e329
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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