Indole → Methyl 3-indoleglyoxylate

HRID 368738

Reaction equation

HRID 368738 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10](Cl)(=O)[C:11](Cl)=[O:12].[CH3:16][O-:17].[Na+].[OH2:19]>CCOCC>[CH3:16][O:17][C:10]([C:11]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:12])=[O:19]

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 65578Oxalyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 588944Methyl 3-indoleglyoxylateYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-65 °C

Procedure

A solution of indole (2.0 g, 1.70 mmol) in Et2O (20 mL) was cooled to 0°-5° C. under N2 and oxalyl chloride (1.5 mL 1.70 mmol) was added dropwise at <5° C. The resultant yellow slurry was stirred 30 min. in the ice bath and was then cooled to -65° C. and a 25% wt. solution of sodium methoxide (7.8 mL, 3.4 mmol) was slowly added at ≤58° C. The reaction was then allowed to warm to room temperature, water was added (10 mL), and the resultant mixture filtered. The solid was dried at room temperature to give 3.21 g (93%) of the titled compound. NMR. MS (FD) m/z=203 (M+, 100%). Analytical calculated for C11H9NO3C, 65.02; H, 4.46; N, 6.89. Found C, 64.93; H, 4.25; N, 7.03.

Workup

  1. temperatureto warm to room temperature
  2. filtrationthe resultant mixture filtered
  3. customThe solid was dried at room temperature

Sources & evidence

ORD record
ord-cf1ed3930221466eaf078ab5091a1085
Source dataset
uspto-grants-2000_10
Patent number
US06133452

Linked notes

Loading…