Oxalyl chloride → (6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester

HRID 250269Notes

Reaction equation

HRID 250269 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].[CH3:24][O-:25].[Na+]>C(OCC)C>[CH3:24][O:25][C:18](=[O:22])[C:19]([C:13]1[C:12]2[C:16](=[CH:17][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)[NH:15][CH:14]=1)=[O:20]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 2608046-(benzyloxy)-1H-indoleHCID 10942334Sodium Methoxide

Product 1

HCID 34181007(6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 0° C. solution of 6-benzyloxyindole (2.10 g, 9.41 mmol) in diethyl ether (20 mL) is treated with oxalyl chloride (1.02 mL, 11.8 mmol). The mixture is stirred for 2 hours while warming to room temperature. The mixture is cooled to −78° C. and sodium methoxide (5.41 mL, 4.35 M) is added. The mixture is warmed up to room temperature over 20 minutes and the reaction is quenched with water (10 mL). The resulting mixture is filtered to obtain the title compound (2.75 g, 95%) as a yellow solid. ES/MS m/e 310.0 (M+1), 308.0 (M−1).

Workup

  1. temperatureThe mixture is cooled to −78° C.
  2. temperatureThe mixture is warmed up to room temperature over 20 minutes
  3. customthe reaction is quenched with water (10 mL)
  4. filtrationThe resulting mixture is filtered

Sources & evidence

ORD record
ord-aa1e9d45db704aaebbfd52b753169a8b
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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