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

HRID 1859957Notes

Reaction equation

HRID 1859957 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[O:15]([CH:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:7][CH:6]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 18625748Ethyl 3-(4-hydroxyphenyl)-2-phenoxypropionate

Product 1

HCID 18625831Ethyl 2-phenoxy-3-[4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl]propionateYield 94%

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 3-(4-hydroxyphenyl)-2-phenoxypropionate (3.33 g), which is the product of Reference example 4(c), 2-(2-bromoethoxy)tetrahydropyran (7.27 g) and potassium carbonate (6.41 g) in dimethylacetamide and the reaction mixture was treated to afford the desired compound (4.53 g) as a syrup.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-cb4fc6abeccd48a29b24dd25da268b6e
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

Loading…