Tetrahydrofuran → Ethyl 5-chloro-3-phenylthioindole-2-carboxylate

HRID 483404

反応式

HRID 483404 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=O)=[CH:5]2.[CH2:16]([Mg]Br)[CH3:17].C1([S:26](=O)(SC2C=CC=CC=2)=O)C=CC=CC=1.O1[CH2:40][CH2:39][CH2:38][CH2:37]1>CCOCC.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[S:26])=[C:5]2[C:17]1[CH:16]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 71031Benzenesulfonothioic acid, S-phenyl esterHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 178418443HCID 178418443、化合物

生成物 1

HCID 86745392Ethyl 5-chloro-3-phenylthioindole-2-carboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 25517Ammonium Chloride溶媒

実験手順

To a cold (0°), stirred solution of ethyl 5-chloroindole-2-carboxylate (223 mg) in 4.5 mL dry tetrahydrofuran, under argon, was added 0.55 mL of a solution of ethylmagnesium bromide in ether. The resultant mixture was stirred for 30 min then cooled to -78°. Solid S-phenyl benzenethiosulfonate (300 mg) was added and the mixture stirred at -78° for 30 min and 0° for 1 h. The mixture was then diluted with ether and saturated aqueous ammonium chloride added. The organic layer was separated, washed with water and brine and dried over MgSO4. Filtration and concentration gave a yellow oil which was purified by flash chromatography on silica gel. Elution with hexane ethyl acetate (85:15) gave the title product. IR (KBr) 3340, 3060, 2994, 1680, 1508, 1263 and 738 cm-1 ; 1H NMR (250 MHz, CDCl3) 6 1.28 (t, 3H, J =7 Hz), 4.39 (q, 2H, J =7 Hz), 7.08-7.24 (m, 5H), 7.27 (dd, 1H, J =9 and 2 Hz), 7.39 (d, 1H, J =9 Hz), 7.60 (d, 1H, J =2 Hz).

後処理

  1. temperaturethen cooled to -78°
  2. additionadded
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and concentration
  7. customgave a yellow oil which
  8. customwas purified by flash chromatography on silica gel
  9. washElution with hexane ethyl acetate (85:15)

出典と根拠

ORDレコード
ord-c4f0e9b1f449489bad167431dfab012a
出典データセット
uspto-grants-1993_07
特許番号
US05225421

関連ノート

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