Trifluoroacetic acid → N-ethoxalyl-2-formyltetrahydroquinoline

HRID 52488ノート

反応式

HRID 52488 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 86750625N-ethoxalyl-2-formyltetrahydroquinoline収率 84%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7833bd2206a14606a599f99825bd66c9
出典データセット
uspto-grants-1997_04
特許番号
US05616586

反応ノート

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