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

HRID 483404

Reaction equation

HRID 483404 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c4f0e9b1f449489bad167431dfab012a
Source dataset
uspto-grants-1993_07
Patent number
US05225421

Linked notes

Loading…