Sodium hydride → Ethyl 2-[1-(3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]pentanoate

HRID 390608Notes

Reaction equation

HRID 390608 reaction equation
[H-].[Na+].[CH3:3][CH2:4][CH2:5][CH:6](P(OCC)(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:20][NH:21][C:22]1[CH:23]=[C:24]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=2)[CH:25]=[CH:26][CH:27]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:20][NH:21][C:22]1[CH:23]=[C:24]([C:28]2[CH:33]=[CH:32][C:31](/[CH:34]=[C:6](\[CH2:5][CH2:4][CH3:3])/[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:30][CH:29]=2)[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 98244Ethyl 2-(diethoxyphosphinyl)pentanoateHCID 13945243'-Methylaminobiphenyl-4-carbaldehyde

Product 1

HCID 68957414Ethyl 2-[1-(3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]pentanoateYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

197 mg (4.9 mmol) of sodium hydride are added to a mixture of 1.2 mL (4.9 mmol) of triethyl 2-phosphonopentanoate and 415 mg of 3′-methylaminobiphenyl-4-carbaldehyde prepared as described in Example 9b (2.0 mmol) in 10 mL of tetrahydrofuran. The reaction mixture is stirred at room temperature overnight. The reaction medium is poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and the residue (1 g) is purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 511 mg (81%) of ethyl 2-[1-(3′-methylaminobiphenyl-4-yl)meth-(E)-ylidene]pentanoate are obtained in the form of a yellow oil.

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is evaporated off
  6. customthe residue (1 g) is purified by chromatography on a column of silica
  7. washeluted with a 90/10 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-5ab98516acda410db98b7a60f5f45592
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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