Trifluoroacetic acid → N-ethoxalyl-2-formyltetrahydroquinoline

HRID 52488노트

반응식

HRID 52488 반응식
[C:1]([N:8]1[C:17]2[CH:12]([CH2:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH:9]1[CH2:18][O:19][Si](C)(C)C)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.FC(F)(F)C(O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([N:8]1[C:17]2[CH:12]([CH2:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH:9]1[CH:18]=[O:19])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67722031N-ethoxalyl-2-trimethylsilyloxymethyltetrahydroquinoline

생성물 1

HCID 86750625N-ethoxalyl-2-formyltetrahydroquinoline수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of N-ethoxalyl-2-trimethylsilyloxymethyltetrahydroquinoline (15.55 g, 50.92 mmol) and Dess-Martin reagent (32.4 g, 76.37 mmol) in dichloromethane (160 mL) in the presence of trifluoroacetic acid (0.8 mL) was stirred for 1 h at room temperature. Aqueous sodium thiosulfate solution and saturated aqueous sodium bicarbonate were added successively and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 11.23 g of N-ethoxalyl-2-formyltetrahydroquinoline (84%): 1H NMR (270 MHz, CDCl3) δ9.57 (s, 1H), 7.19 (m, 4H), 5.07 (t, 1H, J=8 Hz), 4.19 (q, 2H, J=7 Hz), 2.76 (m, 2H), 2.45 (m, 1H), 1.96 (m, 1H), 1.15 (t, 3H, J=7 Hz).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7833bd2206a14606a599f99825bd66c9
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

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