2-Bromoethanol → 2-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethanol

HRID 2037370Notes

Reaction equation

HRID 2037370 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:16][N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[OH:26])[CH3:2].Br[CH2:28][CH2:29][OH:30]>C(O)(C)C.[OH-].[Na+].CC(=O)OCC>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:23])[CH3:24])=[CH:16][N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[O:26][CH2:28][CH2:29][OH:30])[CH3:2]

Participants

6

Reactant 2

HCID 108982-Bromoethanol2×HCID 1363440752-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenol

Product 1

HCID 686309092-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethanolYield 79.8%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of the compound of Example 32 (1.00 g, 2.85 mmol) in isopropanol (10 mL) and 3 M aq. NaOH (3 mL), 2-bromo-ethanol (1.42 g, 11.4 mmol) is added. The mixture is stirred at 60° C. for 24 h before another portion of 2-bromo-ethanol (176 mg, 1.41 mmol) is added. Stirring is continued at 60° C. for 6 h. The mixture is diluted with EA and washed with water. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to 3:1 to give the title compound (900 mg) as a colourless oil; LC-MS: tR=1.10 min, [M+H]+=396.09.

Workup

  1. additionis added
  2. washwashed with water
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to 3:1

Sources & evidence

ORD record
ord-2b1c853e3f5c4631af10271e6abb2398
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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