Ethyl Acetate → 5-Cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid

HRID 252441Notes

Reaction equation

HRID 252441 reaction equation
[C:1]([CH:3](P(OCC)(OCC)=O)[CH:4]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH2:5][CH2:6][C:7]([OH:9])=[O:8])#[N:2].[H-].[Na+].[N+:26]([C:29]1[CH:36]=[CH:35][C:34]([O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:33][C:30]=1[CH:31]=O)([O-:28])=[O:27].C(OCC)(=O)C>C1COCC1>[C:1]([C:3](=[CH:31][C:30]1[CH:33]=[C:34]([O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:35]=[CH:36][C:29]=1[N+:26]([O-:28])=[O:27])[CH:4]([CH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)[CH2:5][CH2:6][C:7]([OH:9])=[O:8])#[N:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 442030822-Nitro-5-phenoxybenzaldehydeHCID 594281685-Cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid

Product 1

HCID 672694525-Cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid (2.68 g, 7.7 mmol) in THF (300 mL), sodium hydride (60%, 1.24 g) was added portionwise at room temperature. 2-Nitro-5-phenoxy-benzaldehyde (1.9 g, 7.7 mmol) was then added, and the reaction mixture was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, and the resulting solution was washed with saturated aqueous NH4Cl solution. The organic phase was separated, dried with MgSO4, and filtered. The filtrate was evaporated in vacuo to yield an oil which was triturated with heptane to yield the title compound as a solid.

Workup

  1. washthe resulting solution was washed with saturated aqueous NH4Cl solution
  2. customThe organic phase was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customto yield an oil which
  7. customwas triturated with heptane

Sources & evidence

ORD record
ord-c6dbd89354154073b916246c7e6fd9b6
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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