Potassium Hydroxide → HCID 57709201, compound

HRID 546841Notes

Reaction equation

HRID 546841 reaction equation
[OH-:1].[K+].[CH2:3]([C:5]([C:26]1[CH:39]=[CH:38][C:29]([O:30][CH2:31][C@@H:32]2[O:36][C:35](=[O:37])[CH2:34][CH2:33]2)=[C:28]([CH3:40])[CH:27]=1)([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]([C:19]([CH2:23][CH3:24])([OH:22])[CH2:20][CH3:21])=[CH:17][CH:18]=2)=[C:10]([CH3:25])[CH:9]=1)[CH2:6][CH3:7])[CH3:4]>O1CCCC1CO>[CH2:6]([C:5]([C:26]1[CH:39]=[CH:38][C:29]([O:30][CH2:31][C@H:32]([OH:1])[CH2:33][CH2:34][C:35]([OH:36])=[O:37])=[C:28]([CH3:40])[CH:27]=1)([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]([C:19]([CH2:20][CH3:21])([OH:22])[CH2:23][CH3:24])=[CH:17][CH:18]=2)=[C:10]([CH3:25])[CH:9]=1)[CH2:3][CH3:4])[CH3:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57708924HCID 57708924, compound

Product 1

HCID 57709201HCID 57709201, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Conditions

Temperature
65 °C

Procedure

A 1 N potassium hydroxide aqueous solution (0.083 mL, 0.083 mmol) was added to a solution of 5(R)-[4-(1-ethyl-1-{4-[5-(1-ethyl-1-hydroxy-propyl)-furan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenoxymethyl]-dihydro-furan-2-one (Example 21-(1); 8.6 mg, 0.017 mmol) in tetrahydrofuran-methanol=10:1 (1.1 mL), and the mixture was stirred at 65° C. for one and half hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform/methanol=10/1, saturated with water) to give the title compound as a colorless oil (8.2 mg, 90%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (chloroform/methanol=10/1, saturated with water)

Sources & evidence

ORD record
ord-18cf7b726b6848f68a76a50ce7c30a9b
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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