Sodium Methoxide → HCID 18354834, compound

HRID 429658Notes

Reaction equation

HRID 429658 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:3]=1[CH:4]=[C:5]([CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:6][C:7]2=[O:8].[CH3:22][O-].[Na+]>CO>[CH2:15]([O:14][CH2:13][C:5]1[NH:1][C:2]2[CH:12]=[CH:11][CH:10]=[C:9]([C:7]([O:6][CH3:22])=[O:8])[C:3]=2[CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18354826HCID 18354826, compound

Product 1

HCID 18354834HCID 18354834, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-amino-3-benzyloxymethylisocoumarin (800 mg) and sodium methylate in methanol (768 mg) was stirred at ambient temperature for 20 minutes. After removal of solvents, water (40 ml) was added to the residue and the whole was extacted with chloroform. The extract was washed with water, dried over magnesium sulfate, and evaporated to dryness to leave a crude product, which was purified by silica gel column chromatography with n-hexane:ethyl acetate (6:1) as an eluent to afford methyl 2-benzyloxymethylindole-4-carboxylate (660 mg).

Workup

  1. customAfter removal of solvents, water (40 ml)
  2. additionwas added to the residue
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customto leave a crude product, which
  7. customwas purified by silica gel column chromatography with n-hexane:ethyl acetate (6:1) as an eluent

Sources & evidence

ORD record
ord-ceab19adee34421c85140c152ff27419
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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