Water → Methyl 5-cyano-5-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxocyclohexanecarboxylate

HRID 1450530Notes

Reaction equation

HRID 1450530 reaction equation
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:17]=1)([CH2:10][CH2:11][C:12]([O:14]C)=O)[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:2].[H-].[Na+].O>COCCOC>[C:6]([CH:5]1[CH2:4][C:3]([C:1]#[N:2])([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:17]=2)[CH2:10][CH2:11][C:12]1=[O:14])([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 10811164Dimethyl 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]heptanedioate

Product 1

HCID 10959646Methyl 5-cyano-5-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxocyclohexanecarboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of dimethyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)pimelate (5.9 g, 14.6 mmol) in dry 1,2-dimethoxyethane (120 mL) under an argon atmosphere was added sodium hydride (80% suspension in mineral oil, 1.05 g, 43.8 mmol). The mixture was heated to reflux for 4.5 h, then was cooled to room temperature and was stirred for 16 h. Water was added and the reaction mixture was partitioned between ether and acidic water. The organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo. The residue was purified by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, to provide a white foam (4.9 g, 93%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4.5 h
  3. customthe reaction mixture was partitioned between ether and acidic water
  4. extractionThe organic extract
  5. dry with materialwas dried (magnesium sulfate)
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with 3:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-ffb7653c763f4d6a8d39c487ec274e76
Source dataset
uspto-grants-1997_02
Patent number
US05602173

Reaction notes

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