Sodium hydride → HCID 18973684, compound

HRID 2399404Notes

Reaction equation

HRID 2399404 reaction equation
[H-].[Na+].[C:3]([C:5]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]([F:29])[F:28])[CH:19]=1)([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:6][CH2:7][C:8]([O:10]C)=O)#[N:4]>COCCOC>[C:14]([CH:13]1[CH2:12][C:5]([C:3]#[N:4])([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]([F:29])[F:28])[CH:19]=2)[CH2:6][CH2:7][C:8]1=[O:10])([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18973709HCID 18973709, compound

Product 1

HCID 18973684HCID 18973684, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of sodium hydride (95%, 0.33 g, 13.2 mmol) in dry 1,2-dimethoxyethane (70 mL) under an argon atmosphere was added a solution of dimethyl 4-cyano-4-(3-difluoromethoxy-4-methoxyphenyl)pimelate (1.7 g. 4.4 mmol) in dry 1,2-dimethoxyethane (70 mL). The resulting mixture was refluxed for 5h, cooled to room temperature, stirred overnight and quenched with water. The mixture was partitioned between ethyl acetate and acidic water, extracted three times with ethyl acetate, the organic layer was dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, provided an oil (0.51 g, 33%, 51% based on recovered starting material).

Workup

  1. customquenched with water
  2. customThe mixture was partitioned between ethyl acetate and acidic water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialthe organic layer was dried (magnesium sulfate)
  5. customthe solvent was removed in vacuo
  6. customPurification by flash chromatography
  7. washeluting with 3:1 hexanes/ethyl acetate
  8. customprovided
  9. customan oil (0.51 g, 33%, 51% based on recovered starting material)

Sources & evidence

ORD record
ord-c535b128b29d4e3784ba11b64f6c1e80
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

Loading…