Potassium Carbonate → 4-(5-Bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid-ethyl ester

HRID 2054932Notes

Reaction equation

HRID 2054932 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([CH3:11])(O)[CH3:9])[CH:7]=1.[CH2:14]([O:16][C:17](=[O:25])[C:18]([O:20][Si](C)(C)C)=[CH2:19])[CH3:15].[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:14]([O:16][C:17](=[O:25])[C:18](=[O:19])[CH2:20][C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:12][CH3:13])([CH3:11])[CH3:9])[CH3:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24287Tin tetrachlorideHCID 111168062-Trimethylsilanyloxy-acrylic acid ethyl esterHCID 219488782-(5-Bromo-2-methoxyphenyl)propan-2-ol

Product 1

HCID 692032244-(5-Bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid-ethyl esterYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9.8 g of 1-(5-bromo-2-methoxyphenyl)-1-methylethanol and 15.24 g of 2-(trimethylsilyloxy)-acrylic acid ethyl ester in 150 ml of dichloromethane are mixed at −70° C. with 5.6 ml of tin tetrachloride. After 20 minutes at −70° C., the solution is poured onto a semi-saturated potassium carbonate solution and mixed with dichloromethane. The dichloromethane phase is washed with potassium carbonate solution, 1 M hydrochloric acid and water, dried (Na2SO4) and concentrated by evaporation. After bulb tube distillation, 5.2 g of 4-(5-bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid-ethyl ester is obtained. Boiling point: 160° C./0.04 hPa

Workup

  1. washThe dichloromethane phase is washed with potassium carbonate solution, 1 M hydrochloric acid and water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. distillationAfter bulb tube distillation

Sources & evidence

ORD record
ord-a91dd0904abf475cb4a2b79c47437880
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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