Sodium hydride → HCID 18973684, compound

HRID 1780832Notes

Reaction equation

HRID 1780832 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 5 h, 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. temperatureThe resulting mixture was refluxed for 5 h
  2. customquenched with water
  3. customThe mixture was partitioned between ethyl acetate and acidic water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialthe organic layer was dried (magnesium sulfate)
  6. customthe solvent was removed in vacuo
  7. customPurification by flash chromatography
  8. washeluting with 3:1 hexanes/ethyl acetate
  9. customprovided
  10. customan oil (0.51 g, 33%, 51% based on recovered starting material)

Sources & evidence

ORD record
ord-8d4090f739e8442c89d61a67d2edcc18
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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