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

HRID 1956756노트

반응식

HRID 1956756 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-696304ab7f56471da8dca1659c725b48
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05780633

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