Dimethylformamide → HCID 18467871, compound

HRID 2229490Notes

Reaction equation

HRID 2229490 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][CH2:6][CH:7](Cl)CC.[H-].[Na+].CN(C=[O:26])C>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:4]2([C:3]([OH:2])=[O:19])[CH2:5][CH2:6][CH2:7][O:26]2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 70074500HCID 70074500, compound

Product 1

HCID 18467871HCID 18467871, compound

Procedure

To a solution of 5-chloro-2-(4-methoxyphenyl)-heptanoic acid methyl ester (0.26 g, 0.96 mmol) in 5 ml of DMF at 0° C. was added sodium hydride (0.6 g, 1.4 mmol). The reaction was stirred for 1 h at this temperature then quenched with 10 ml of water. The product was extracted into ethyl acetate (3×15 ml), washed with brine (20 ml), dried with magnesium sulfate and concentrated in vacuo to give a yellow oil. Silica gel chromatography eluting with hexane/ethyl acetate (4:1) gave 0.063 g of the title compound as a colorless oil.

Workup

  1. customthen quenched with 10 ml of water
  2. extractionThe product was extracted into ethyl acetate (3×15 ml)
  3. washwashed with brine (20 ml)
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. washSilica gel chromatography eluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-d81f78ab4ff64f7c8529cdb12978bef9
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

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