Acetic Acid → 4-[1-(S)-(4-isobutylphenyl)butoxy]phenyl 2-pyridylmethyl ketone

HRID 1956756Notes

Reaction equation

HRID 1956756 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][C:20]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C@H:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])=[CH:6][CH:7]=2)[CH2:12][CH2:13][CH3:14])=[CH:25][CH:24]=1)=[O:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 79752-MethylpyridineHCID 2733832Lithium HexamethyldisilazideHCID 18663759methyl 4-[1-(S)-(4-isobutylphenyl)butoxy]benzoate

Product 1

HCID 186637584-[1-(S)-(4-isobutylphenyl)butoxy]phenyl 2-pyridylmethyl ketone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-[1-(S)-(4-isobutylphenyl)-butoxy]benzoate (283 mg) and 2-methylpyridine (0.09 ml) in tetrahydrofuran (5 ml) was added 1.0M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (2.7 ml) at 0° C. The mixture was stirred for 18 hours at room temperature. Acetic acid (0.18 ml) and ethyl acetate (15 ml) was added to the mixture. The mixture was washed with water and aqueous solution of sodium bicarbonate, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1) to give 4-[1-(S)-(4-isobutylphenyl)butoxy]phenyl 2-pyridylmethyl ketone as a yellow oil (216 mg).

Workup

  1. washThe mixture was washed with water and aqueous solution of sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-696304ab7f56471da8dca1659c725b48
Source dataset
uspto-grants-1998_07
Patent number
US05780633

Reaction notes

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