Sodium hydride → methyl (E)-2-[2-(4-cyclopropylmethoxy-3,5-dichlorophenoxymethyl)phenyl]-3-methoxyacrylate

HRID 2115581Notes

Reaction equation

HRID 2115581 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([Cl:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]=2[Cl:14])[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1/[C:25](=[CH:30]\[O:31][CH3:32])/[C:26]([O:28][CH3:29])=[O:27]>CN(C)C=O.O>[CH:1]1([CH2:4][O:5][C:6]2[C:7]([Cl:14])=[CH:8][C:9]([O:13][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3/[C:25](=[CH:30]\[O:31][CH3:32])/[C:26]([O:28][CH3:29])=[O:27])=[CH:10][C:11]=2[Cl:12])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylateHCID 693031644-Cyclopropylmethoxy-3,5-dichlorophenol

Product 1

HCID 11561176methyl (E)-2-[2-(4-cyclopropylmethoxy-3,5-dichlorophenoxymethyl)phenyl]-3-methoxyacrylateYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 4-cyclopropylmethoxy-3,5-dichlorophenol (1.54 g; 6.6 mmoles) in DMF (5 ml) is added dropwise, at 0° C., to a suspension of sodium hydride (0.16 g; 6.6 mmoles) in N,N-dimethyl formamide (DMF; 5 ml). The mixture is kept under stirring at room temperature for 30 minutes and a solution of methyl (E)-2-(2bromomethylphenyl)-3-methoxyacrylate (1.9 g; 6.6 mmoles) in DMF (5 ml) is then added. The mixture is kept under stirring for 4 hours; the mixture is diluted with water (40 ml) and an extraction is effected with ethyl acetate (3×25 ml). The organic phases are joined, washed with water (2×20 ml), dried with sodium sulfate, filtered and concentrated at reduced pressure. The raw product obtained is purified by means of silica gel chromatography, eluting with hexane/ethyl acetate 9:1. 1.9 g of the desired product (thick oil) are obtained.

Workup

  1. stirringunder stirring for 4 hours
  2. extractionan extraction
  3. washwashed with water (2×20 ml)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe raw product obtained
  8. customis purified by means of silica gel chromatography
  9. washeluting with hexane/ethyl acetate 9:1

Sources & evidence

ORD record
ord-550849ed0216449aa052b48ae2c4fce0
Source dataset
uspto-grants-2008_10
Patent number
US07435844B2

Reaction notes

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