Water → HCID 87294983, compound

HRID 1918347Notes

Reaction equation

HRID 1918347 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:8]([CH:11](Br)Br)=[CH:9][CH:10]=1)=[O:4].[OH2:24]>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:8]([CH:11]=[O:24])=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 2

HCID 962WaterHCID 67168908HCID 67168908, compound

Product 1

HCID 87294983HCID 87294983, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent2×

Procedure

The compound of step 2 (2.1 g, 4.65 mmol) was dissolved in acetonitrile (25 ml). Silver nitrate (1.97 g, 11.6 mmol) was dissolved in water (3 ml) and this solution was added to the acetonitrile solution. This mixture was stirred for 1 h in reflux. Acetonitrile was evaporated in vacuo, the remainder was partitioned between ethyl acetate and water, the combined organic extracts were dried over sodium chloride, filtered over a small plug of silica and evaporated to dryness. A crystalline crop was yielded on addition of methanol and filtration. The mother liquor was evaporated to dryness and purified by silica gel chromatography with a heptane/ethyl acetate gradient to yield a second crop. Both were combined to yield the title compound (1.0 g).

Workup

  1. temperaturein reflux
  2. customAcetonitrile was evaporated in vacuo
  3. customthe remainder was partitioned between ethyl acetate and water
  4. dry with materialthe combined organic extracts were dried over sodium chloride
  5. filtrationfiltered over a small plug of silica
  6. customevaporated to dryness
  7. customA crystalline crop was yielded on addition of methanol and filtration
  8. customThe mother liquor was evaporated to dryness
  9. custompurified by silica gel chromatography with a heptane/ethyl acetate gradient
  10. customto yield a second crop

Sources & evidence

ORD record
ord-fa5b89b08a8a496fac135911cd3cd914
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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