Water → HCID 69913992, compound

HRID 843507Notes

Reaction equation

HRID 843507 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[H-].[Na+].C1(C)C(C([O:21][C@@H:22]2[C@@H:26]([CH2:27][O:28]C(C3C(C)=CC=CC=3)=O)[O:25][C@H:24](Cl)[CH2:23]2)=O)=CC=CC=1.O>CN(C)C=O>[O:10]([C:3]1[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=1)[C@@H:24]1[O:25][C@H:26]([CH2:27][OH:28])[C@@H:22]([OH:21])[CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 69913967HCID 69913967, compound

Product 1

HCID 69913992HCID 69913992, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-Nitrophenol (178 mg, 1.28 mmol) and sodium hydride (64 mg of a 60% dispersion in mineral oil, 1.6 mmol) were stirred together in dry dimethylformamide (4 ml) at room temperature for 30 minutes then the chloride (416 mg, 1.07 mmol) from Example 16 was added. The mixture was stirred for a further 3 hours, then water (100 ml) was added and the mixture was evaporated in vacuo. The residue was purified by flash chromatography on silica gel (eluting with 20% ethyl acetate in hexanes) to give a pale yellow oil which crystallized from a mixture of chloroform and hexanes to give the title compound as a colourless solid (190 mg, 36%).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (eluting with 20% ethyl acetate in hexanes)
  3. customto give a pale yellow oil which
  4. customcrystallized from a mixture of chloroform and hexanes

Sources & evidence

ORD record
ord-95e842ac672e4e8ebf25cbbb9867e479
Source dataset
uspto-grants-2002_04
Patent number
US06379911B2

Reaction notes

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