Water → HCID 14986696, compound

HRID 465599Notes

Reaction equation

HRID 465599 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=2)[CH:2]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].Br[CH2:30][CH2:31][CH2:32][CH2:33][Cl:34].O>CN(C)C=O.O1CCCC1>[Cl:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:8]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 813641-Bromo-4-chlorobutaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 14986695Ethyl [3-(pyridin-3-yl)phenyl]acetate

Product 1

HCID 14986696HCID 14986696, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.363 g (1.5 mmol) of ethyl m-(3-pyridyl)-phenylacetate in 5.4 ml dry dimethylformamide at 5° is added 1.56 ml of a 1M solution of sodium hexamethyldisilazide in tetrahydrofuran. The organic layer is evaporated to dryness and resulting orange colored solution is stirred for 10 min and 0.54 ml (4.7 mmol) 1-bromo-4-chlorobutane is added rapidly. The reaction mixture is stirred at 5° for 2 h and then poured into water and extracted thrice with ether. The organic layer is evaporated to dryness and the resulting oil is purified by flash chromatography using 1:1 ether/hexane to obtain ethyl 6-chloro-2-[m-(3-pyridyl)-phenyl]-hexanoate; IR (CH2Cl2): 1728, 1278, 1184, 1165, 1023 cm-1.

Workup

  1. customThe organic layer is evaporated to dryness
  2. customresulting orange colored solution
  3. stirringThe reaction mixture is stirred at 5° for 2 h
  4. extractionextracted thrice with ether
  5. customThe organic layer is evaporated to dryness
  6. customthe resulting oil is purified by flash chromatography

Sources & evidence

ORD record
ord-2c0f3146c9584ef2b559c009052f4588
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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