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

HRID 1859972Notes

Reaction equation

HRID 1859972 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]([CH2:13][CH2:14][CH2:15][CH3:16])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.Br[CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH2:13]([CH:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[CH:18][CH:17]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 18625817Ethyl 2-(4-hydroxybenzyl)caproate

Product 1

HCID 18625771Ethyl 2-butyl-3-[4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl]propionateYield 83.7%

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-(4-hydroxybenzyl)caproate (2.40 g), which is the product of Reference example 6(c), 2-(2-bromoethoxy)tetrahydropyran (1.63 g) and potassium carbonate (3.23 g) in dimethylacetamide and the reaction mixture was treated to afford the desired compound (2.47 g) as a syrup.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-0fdd8e4c408945b299186f43b21c6281
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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