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

HRID 1956756ノート

反応式

HRID 1956756 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-696304ab7f56471da8dca1659c725b48
出典データセット
uspto-grants-1998_07
特許番号
US05780633

反応ノート

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