Allyl bromide → 2-allyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide

HRID 643236Notes

Reaction equation

HRID 643236 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][CH:6]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]#[CH:21])=[C:14]([O:22][CH3:23])[CH:13]=1)=[O:8].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:1]([O:5][CH:6]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]#[CH:21])=[C:14]([O:22][CH3:23])[CH:13]=1)=[O:8])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 59260584HCID 59260584, compound

Product 1

HCID 592605832-allyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Allyl bromide (1.2 g, 10 mmol) is added slowly at room temperature to a mixture of 2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide (3.0 g, 8.2 mmol), 30% sodium hydroxide solution (6.5 ml, 41 mmol) and catalytic amounts of tetrabutylammonium bromide (50 mg) in 30 ml of dichloromethane. The reaction is stirred for 16 hours at +40° C. Subsequently the mixture is evaporated and the residue is diluted with water and dichloromethane. The phases are separated and the aqueous phase is extracted three times with dichloromethane. The combined organic layer is washed with brine, dried over sodium sulfate and evaporated. The remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 1:1) to give 2-allyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide (E1.17).

Workup

  1. customSubsequently the mixture is evaporated
  2. additionthe residue is diluted with water and dichloromethane
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted three times with dichloromethane
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-7b2d5379a07e4769a2a07c0e199e8ffc
Source dataset
uspto-grants-2010_04
Patent number
US07700522B2

Reaction notes

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