Benzyl chloroformate → 1-Benzyloxycarbonyl-5-chloro-3-formylindol

HRID 2227520Notes

Reaction equation

HRID 2227520 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[O:12].[H-].[Na+].[C:15](Cl)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>O1CCCC1>[CH2:18]([O:17][C:15]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[C:5]([CH:11]=[O:12])=[CH:6]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 27953745-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 184739871-Benzyloxycarbonyl-5-chloro-3-formylindol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-3-formylindole (5.00 g) in tetrahydrofuran (135 ml) was added sodium hydride (60% oil suspension, 3.53 g). The mixture was stirred for 20 minutes at room temperature. Carbobenzoxychloride (6.64 ml) was added to the mixture. After being stirred for 1 hour at room temperature, the whole was poured into ice water. The mixture was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solution was concentrated to give a residue, which was subjected to silica gel chromatography. Elution with hexane-ethyl acetate (5:1) provided 1-benzyloxycarbonyl-5-chloro-3-formylindol (5.74 g) as a crystal.

Workup

  1. stirringAfter being stirred for 1 hour at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated
  6. customto give a residue, which
  7. washElution with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-8f5c9c6849e442b09051d7787c265e50
Source dataset
uspto-grants-2002_07
Patent number
US06414003B1

Reaction notes

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