Sodium hydride → HCID 90387563, compound

HRID 2170202Notes

Reaction equation

HRID 2170202 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].Cl[Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17]>O1CCCC1>[CH3:1][C:2]1[N:3]([Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylateHCID 139400Triisopropylsilyl chloride

Product 1

HCID 90387563HCID 90387563, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-methyl-1H-pyrrole-3-carboxylate (1 g, 6.53 mmol) in tetrahydrofuran (15 mL) at 0° C. was treated with sodium hydride (60% oil dispersion, 0.39 g, 9.8 mmol), stirred for twenty minutes, and then treated with chlorotriisopropylsilane (1.676 mL, 7.83 mmol). The reaction mixture was stirred for three hours and allowed to reach ambient temperature. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 1-8% ethyl acetate in hexanes) to give 1.85 g (91%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred for three hours
  2. customto reach ambient temperature
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (silica gel, 1-8% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-45573faa9e3b4fd39762ddb67ddf90ca
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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