Methanol → Methyl 2-(6-ethyl-1H-indol-3-yl)oxoacetate

HRID 2215825Notes

Reaction equation

HRID 2215825 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].C(Cl)Cl.[CH2:10]([C:12]1[CH:20]=[C:19]2[C:15]([CH:16]=[CH:17][NH:18]2)=[CH:14][CH:13]=1)[CH3:11].[CH3:21][O-:22].[Na+].CO>CCOCC>[CH2:10]([C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:1](=[O:5])[C:2]([O:22][CH3:21])=[O:3])=[CH:17][NH:18]2)=[CH:14][CH:13]=1)[CH3:11]

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 10942334Sodium MethoxideHCID 183302676-ethyl-1H-indole

Product 1

HCID 21949969Methyl 2-(6-ethyl-1H-indol-3-yl)oxoacetateYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 2.0 M solution of oxalyl chloride in methylene chloride (4.75 mL, 9.6 mmol) was added to a solution of 6-ethylindole (1.39 g, 9.6 mmol) in ether (20 mL) dropwise over 10 min at 4° C. under N2. The ice bath was removed and the resulting mixture was stirred for 2 h. A 25% sodium methoxide in methanol solution (4.3 mL, 18.8 mmol) was added at −78° C. over 5 min. The mixture was allowed to warm up to room temperature and stirred for 1 h. The reaction was quenched with water (10 mL), filtered and rinsed with cold ether to afford the title compound (1.34, 72%) as a yellow solid. 1H NMR (CDCl3) δ 9.07 (bs, 1H), 8.43 (m, 1H), 8.32 (m, 1H), 7.29–7.21 (m, 2H), 3.95 (m, 3H), 2.78 (m, 2H), 1.29 (m, 3H).

Workup

  1. customThe ice bath was removed
  2. stirringstirred for 1 h
  3. customThe reaction was quenched with water (10 mL)
  4. filtrationfiltered
  5. washrinsed with cold ether

Sources & evidence

ORD record
ord-96371b9802d34546a2127c79be73933c
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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