Sodium hydride → HCID 53818427, compound

HRID 2305634Notes

Reaction equation

HRID 2305634 reaction equation
[C:1]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[F:18][C:19]1[C:20]([N+:28]([O-:30])=[O:29])=[C:21]([O:26][CH3:27])[CH:22]=[C:23](F)[CH:24]=1>CN1C(=O)CCC1>[F:18][C:19]1[CH:24]=[C:23]([CH:2]([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[C:1]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:22]=[C:21]([O:26][CH3:27])[C:20]=1[N+:28]([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68324Di-tert-butyl malonateHCID 103301291,5-Difluoro-3-methoxy-2-nitrobenzene

Product 1

HCID 53818427HCID 53818427, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Di-t-butyl malonate(18 g) was added dropwise to a stirred suspension of sodium hydride[60% dispersion in mineral oil](3.3 g) in N-methyl pyrrolidinone(100 mL) under an atmosphere of argon and the mixture was stirred until effervescence ceased. 3,5 Difluoro-2-nitro-anisole(6.4 g) was added and the mixture was stirred at 80° C. for 2 h. The mixture was cooled to room temperature then partitioned between water and ether and then the ether extract was dried and evaporated to dryness. The residue was subjected to flash chromatography eluting with increasingly polar mixtures of ethyl acetate and hexane to give the product(5.5 g)

Workup

  1. stirringthe mixture was stirred at 80° C. for 2 h
  2. customthen partitioned between water and ether
  3. extractionthe ether extract
  4. customwas dried
  5. customevaporated to dryness
  6. washeluting
  7. temperaturewith increasingly polar mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c487fb3c7af94d81a27d1729ddc9e115
Source dataset
uspto-grants-2002_08
Patent number
US06441012B1

Reaction notes

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