Ethyl bromoacetate → {2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethoxy}-acetic acid ethyl ester

HRID 1785582Notes

Reaction equation

HRID 1785582 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[C:5]([C:12]1[CH:21]=[CH:20][C:15]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[Na+].[CH3:30][CH2:31][O:32][C:33]([CH2:35]Br)=[O:34]>O1CCCC1>[CH2:31]([O:32][C:33](=[O:34])[CH2:35][O:19][CH2:18][CH2:17][O:16][C:15]1[CH:14]=[CH:13][C:12]([C:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[C:4]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:3][CH2:2][Cl:1])=[CH:21][CH:20]=1)[CH3:30]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 1481272-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol2×

Product 1

HCID 69038968{2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethoxy}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethanol (Compound II) (0.3 g, 0.79 mmol) was dissolved in tetrahydrofuran (5 ml) under a nitrogen atmosphere. Sodium hydride (0.058 g, 1.21 mmol) was added in THF (5 ml) to the solution and the mixture was stirred at room temperature for an hour. Then the mixture was cooled to 0° C., ethyl bromo acetate (0.4 g, 2.38 mmol) was added and the stirring was continued for 5 hours at 0-5° C. The mixture was allowed to warm up to room temperature and stirring was continued overnight. Then the reaction is quenched with water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. The organic phase was washed with water, dried with sodium sulphate and evaporated to dryness. The residue was used in the next reaction step without further purification.

Workup

  1. temperatureThen the mixture was cooled to 0° C.
  2. temperatureto warm up to room temperature
  3. stirringstirring
  4. waitwas continued overnight
  5. customThen the reaction is quenched with water and ethyl acetate
  6. customThe aqueous layer was separated
  7. extractionextracted with ethyl acetate
  8. washThe organic phase was washed with water
  9. dry with materialdried with sodium sulphate
  10. customevaporated to dryness
  11. customThe residue was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-86bfba567d944b9db0ebec0b831653d9
Source dataset
uspto-grants-2009_03
Patent number
US07504530B2

Reaction notes

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