Sodium hydride → HCID 20325833, compound

HRID 372602Notes

Reaction equation

HRID 372602 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH2:14]([O:21][CH2:22]Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>COCCOCCOC>[CH2:14]([O:21][CH2:22][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 18370696HCID 18370696, compound

Product 1

HCID 20325833HCID 20325833, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63 mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376 mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530 mg). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg, 46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N--CH2 --), 5.47 (--OCH2 --), 2.70 (--Ph).

Workup

  1. stirringthe mixture stirred at room temperature for a further 3 hr
  2. filtrationThe suspension was filtered
  3. customthe filtrate evaporated
  4. washThe residue, in ether, was washed with sodium bicarbonate solution, water
  5. customdried
  6. customEvaporation
  7. customgave the crude product as a brown oil (530 mg)
  8. customPurification by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-7c4488014b664ef88c573ae2abfe8b70
Source dataset
uspto-grants-1978_05
Patent number
US04091209

Reaction notes

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