Sodium hydride → HCID 21867387, compound

HRID 857310Notes

Reaction equation

HRID 857310 reaction equation
[Br:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[Br:1][C:2]1[N:3]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 21867385HCID 21867385, compound

Product 1

HCID 21867387HCID 21867387, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a vigorously stirred solution of 0.32 g of the product from Step 2 in 5 mL of DMF was added sequentially 0.045 g NaH (60% in mineral oil), 0.2 mL of ethyl 4-bromobutyrate and 0.02 g of n-Bu4NI. The mixture was stirred for 45 minutes at room temperature, quenched with 5 mL of saturated aqueous solution of NH4Cl and 5 mL of water, and extracted with 40 mL of 1:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated. The residue was purified by silica gel flash chromatography eluted with 9:1 hexane/EtOAc to give 0.3 g of the title compound as an oil.

Workup

  1. customquenched with 5 mL of saturated aqueous solution of NH4Cl and 5 mL of water
  2. extractionextracted with 40 mL of 1:1 hexane/EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluted with 9:1 hexane/EtOAc

Sources & evidence

ORD record
ord-f7ee5e731f9c47eeba2e337270511c6f
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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