Potassium Carbonate → Ethyl 2-butyl-2-methyl-3-[4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl]propionate

HRID 1860002Notes

Reaction equation

HRID 1860002 reaction equation
[CH2:1]([C:5]([CH3:19])([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH2:3][CH3:4].Br[CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH2:1]([C:5]([CH3:19])([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:21][CH2:22][O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[CH:16][CH:17]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 18625949Ethyl 2-butyl-3-(4-hydroxyphenyl)-2-methylpropionate

Product 1

HCID 18625755Ethyl 2-butyl-2-methyl-3-[4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl]propionateYield 95.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In a similar manner to that described in Reference example 3(e), a reaction was carried out using ethyl 2-butyl-3-(4-hydroxyphenyl)-2-methylpropionate (2.95 g), which is the product of Reference example 10(b), 2-(2-bromoethoxy)tetrahydropyran (4.66 g) and potassium carbonate (4.62 g) in dimethylacetamide and the reaction mixture was treated to afford the desired compound (4.18 g) as a syrup.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-5f1f61735c3945b6a971abb089df03fc
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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