Sodium hydride → HCID 15295197, compound

HRID 2399407Notes

Reaction equation

HRID 2399407 reaction equation
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH:26]2[CH2:28][CH2:27]2)[CH:17]=1)([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:4][CH2:5][C:6](OC)=[O:7])#[N:2].[H-].[Na+]>COCCOC>[C:12]([CH:11]1[CH2:10][C:3]([C:1]#[N:2])([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28]3)[CH:17]=2)[CH2:4][CH2:5][C:6]1=[O:7])([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18973704HCID 18973704, compound

Product 1

HCID 15295197HCID 15295197, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of dimethyl 4-cyano-4-(3-cyclopropylmethoxy-4-methoxyphenyl)pimelate (10.4 g, 26.7 mmol) in dry 1,2-dimethoxyethane (500 mL) under an argon atmosphere was added sodium hydride (80% dispersion in mineral oil, 2.5 g, 31.2 mmol). The resulting mixture was refluxed for 4 h, cooled to room temperature and quenched with water. The mixture was partitioned between ethyl acetate and acidic water, extracted three times, the organic layer was dried (magnesium sulfate) and the solvent was removed in vacuo. The product was purified by flash chromatography, eluting with 2:1 hexanes/ethyl acetate, to provide an oil (9 g, 95%).

Workup

  1. temperatureThe resulting mixture was refluxed for 4 h
  2. customquenched with water
  3. customThe mixture was partitioned between ethyl acetate and acidic water
  4. extractionextracted three times
  5. dry with materialthe organic layer was dried (magnesium sulfate)
  6. customthe solvent was removed in vacuo
  7. customThe product was purified by flash chromatography
  8. washeluting with 2:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-7a04bde916184e558ec2a026b315edad
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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