Dimethylformamide → HCID 18433373, compound

HRID 2305626Notes

Reaction equation

HRID 2305626 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:20])[CH:12]=[C:13]([O:18][CH3:19])[C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35]>C(OCC)(=O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:13]([O:18][CH3:19])[C:14]=1[N+:15]([O-:17])=[O:16])[O:20][CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 184333963-Benzyloxy-5-methoxy-4-nitrophenol

Product 1

HCID 18433373HCID 18433373, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-benzyloxy-5-methoxy-4-nitrophenol(3.85 g), N,N-dimethyl formamide (20 mL), potassium carbonate(2.8 g) and methyl bromoacetate(2.42 g) was stirred at ambient temperature for 3 h. The mixture was treated with water and ethyl acetate and the organic phase was separated, washed with brine, dried and evaporated to dryness. The residue was purified by flash chromatography eluting with increasingly polar mixtures of ethyl acetate and hexane to give the product (4.6 g), (m/e348, MH+).

Workup

  1. customthe organic phase was separated
  2. washwashed with brine
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography
  6. washeluting
  7. temperaturewith increasingly polar mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-e4c30e3988e0444184b715e7f7d0c6ad
Source dataset
uspto-grants-2002_08
Patent number
US06441012B1

Reaction notes

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