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

HRID 483404노트

반응식

HRID 483404 반응식
[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

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 71031S-Phenyl benzenethiosulphonateHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 178418443HCID 178418443, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 25517Ammonium Chloride용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c4f0e9b1f449489bad167431dfab012a
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05225421

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