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

HRID 252469Notes

Reaction equation

HRID 252469 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].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:34]([O:36][C:37]1[C:44]([O:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH:43][C:40]([CH:41]=O)=[C:39]([N+:52]([O-:54])=[O:53])[CH:38]=1)[CH3:35].O>C1COCC1>[C:1]([C:3](=[CH:41][C:40]1[CH:43]=[C:44]([O:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:37]([O:36][CH2:34][CH3:35])=[CH:38][C:39]=1[N+:52]([O-:54])=[O:53])[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 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 574757244-Ethoxy-2-nitro-5-phenoxy-benzaldehydeHCID 594281685-Cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid

Product 1

HCID 672684215-Cyano-6-(4-ethoxy-2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid (174 mg, 0.5 mmol) prepared as described in Example 3 above, in THF (10 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1.2 mL, 1.2 mmol). The resulting mixture was stirred for 30 min at −78° C. and then warmed to room temperature. 4-Ethoxy-2-nitro-5-phenoxy-benzaldehyde (137 mg, 0.5 mmol) was added and the resulting mixture stirred for 4 h at room temperature. Water was added, and the resulting solution was extracted with methylene chloride (3×), washed with brine, dried over Na2SO4, filtered and concentrated. The resulting crude mixture was purified by chromatography (silica gel, 0-2% methanol in methylene chloride) to yield a yellow foam.

Workup

  1. temperaturewarmed to room temperature
  2. stirringthe resulting mixture stirred for 4 h at room temperature
  3. extractionthe resulting solution was extracted with methylene chloride (3×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude mixture was purified by chromatography (silica gel, 0-2% methanol in methylene chloride)
  9. customto yield a yellow foam

Sources & evidence

ORD record
ord-0091be64193c4364964fd67218252dd8
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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