HCID 25131666, compound → HCID 25132009, compound

HRID 1616345Notes

Reaction equation

HRID 1616345 reaction equation
[CH3:1][Li].[CH:3]1([C:9]2[CH:10]=[N:11][O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>C1COCC1>[CH:3]1([C:9]2[CH:10]=[N:11][O:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([C:20]([OH:22])([CH3:1])[CH3:21])=[CH:18][CH:19]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 25131666HCID 25131666, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 25132009HCID 25132009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl lithium (159 μL, 1.6 M solution in Et2O, 0.25 mmol) was added dropwise to a solution of 1-(4-(4-cyclohexylisoxazol-5-yl)phenyl)ethanone obtained above (57 mg, 0.21 mmol) in THF (2 mL) at 0° C. After stirring for 15 min, another 100μL of the methyl lithium solution was added to the reaction mixture. After being stirred for an additional 1 h at 0° C., the mixture was quenched with saturated aqueous NH4Cl and diluted with EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with NaCl, dried with magnesium sulfate, filtered and concentrated in vacuo to give a yellow oil. The crude material was purified by flash column chromatography (20%→40% EtOAc/hexanes) to afford 2-(4-(4-cyclohexylisoxazol-5-yl)phenyl)propan-2-ol as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.62 (m, 4H), 2.77 (m, 1H), 2.09 (m, 1H), 1.86 (m, 5H), 1.63 (s, 6H), 1.37 (m, 5H).

Workup

  1. stirringAfter being stirred for an additional 1 h at 0° C.
  2. customthe mixture was quenched with saturated aqueous NH4Cl
  3. additiondiluted with EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic layers were washed with NaCl
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a yellow oil
  10. customThe crude material was purified by flash column chromatography (20%→40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-924258bb52f248d7b50b81c92e45b35a
Source dataset
uspto-grants-2014_07
Patent number
US08765788B2

Reaction notes

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