Water → HCID 23113880, compound

HRID 2376331Notes

Reaction equation

HRID 2376331 reaction equation
[CH:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][C:9]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:10]=2[O:11][CH2:12][C:13](N2CC2C)=[O:14])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:27]([Mg]Br)[CH2:28][CH3:29].O>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:10]=2[O:11][CH2:12][C:13](=[O:14])[CH2:27][CH2:28][CH3:29])=[CH:25][CH:26]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 23114148HCID 23114148, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 23113880HCID 23113880, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-((2-(4-isopropylbenzyl)-3,5-dimethylphenoxy)acetyl)-2-methylaziridine obtained in Reference Example 166 (1.0 g, 2.85 mmol) in THF (20 mL) was added dropwise n-propylmagnesium bromide (a 2.0 M THF solution, 1.43 mL, 2.85 mmol) under argon atmosphere with ice-cooling, and the mixture was stirred for 30 minutes. The reaction solution was warmed to room temperature, water was added thereto, which was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 920 mg (yield 95%) of the title compound. Oily matter.

Workup

  1. temperaturecooling
  2. extractionwhich was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationwas concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-c8621b1c37b14e7db35bfb9aadb92bb6
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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