Sodium hydride → HCID 18355318, compound

HRID 429615Notes

Reaction equation

HRID 429615 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH:5]=[CH:4]1.[C:22]([O:28][CH2:29]Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[C:22]([O:28][CH2:29][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH:5]=[CH:4]1)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 17933207HCID 17933207, compound

Product 1

HCID 18355318HCID 18355318, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (174 mg) in tetrahydrofuran (8.0 ml) was added dropwise a solution of benzyl indole-7-carboxylate (700 mg) in tetrahydrofuran (7.0 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hour. Chloromethyl pivalate (461 mg) was added to the mixture and the solution was stirred at ambient temperature for 3 hours. The reaction was quenched with 1N hydrochloric acid and then the aqueous solution was extracted with ethyl acetate. Drying, filtering and removal of solvents afforded benzyl 1-pivaloyloxymethylindole-7-carboxylate (1.08 g) as a yellow oil.

Workup

  1. stirringthe solution was stirred at ambient temperature for 3 hours
  2. customThe reaction was quenched with 1N hydrochloric acid
  3. extractionthe aqueous solution was extracted with ethyl acetate
  4. customDrying
  5. filtrationfiltering
  6. customremoval of solvents

Sources & evidence

ORD record
ord-31a1f7250e804faf9f2bdbc2c248fbc7
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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