Dichloromethane → HCID 76494514, compound

HRID 1249921Notes

Reaction equation

HRID 1249921 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:10][CH:9]=2)=[O:5])C.[Mg].ClCCl>CO>[CH3:1][O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=2)[NH:7]1)=[O:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 95721Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylateHCID 5462224Magnesium

Product 1

HCID 76494514HCID 76494514, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
7.5 °C

Procedure

5-Benzyloxyindole-2-carboxylic acid ethylester (3 g, 10.1 mmol) and magnesium turnings (1.2 g, 50 mmol) were suspended in dried methanol (180 mL). This mixture was stirred at 5-10° C. under nitrogen for 3 hours, then poured into dichloromethane, and washed with saturated ammonium chloride solution. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulphate and evaporated to leave a brown solid which was further purified by column chromatography (silica gel, dichloromethane) to afford a white solid.

Workup

  1. washwashed with saturated ammonium chloride solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. customevaporated
  6. customto leave a brown solid which
  7. customwas further purified by column chromatography (silica gel, dichloromethane)
  8. customto afford a white solid

Sources & evidence

ORD record
ord-ebc618a576fc48beab4b68a08290496d
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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