Water → HCID 68495256, compound

HRID 1038752Notes

Reaction equation

HRID 1038752 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH3:25][O:26][CH2:27]Cl.O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][O:26][CH3:27])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 46311262HCID 46311262, compound

Product 1

HCID 68495256HCID 68495256, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-benzyloxy-1H-indole-2-carboxylic acid ethyl ester (3.00 g, 10 mmol) in DMF (30 ml) was added 60% sodium hydride in oil (0.49 g, 12 mmol) under ice cooling and the mixture was stirred for 15 minutes. Then to the mixture was added chloromethyl methyl ether (1.0 ml, 13 mmol) under ice cooling and stirred for 0.5 hour. Water (60 ml) was added to the reaction mixture and extracted with AcOEt, the organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous sodium sulfate and evaporated to give the title compound (3.45 g) as a pale brown oil.

Workup

  1. stirringstirred for 0.5 hour
  2. extractionextracted with AcOEt
  3. washthe organic layer was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d15e676944bd4701bcde86bb96271ea2
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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