Acetic Acid → (1R)-1-[5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethyl acetate

HRID 452658

反応式

HRID 452658 の反応式
[F:1][C:2]([F:28])([F:27])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:23][C:22]([C@@H:24]([OH:26])[CH3:25])=[N:21][N:20]=4)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[C:29](O)(=[O:31])[CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[C:29]([O:26][C@@H:24]([C:22]1[O:23][C:19]([C:16]2[CH:17]=[CH:18][C:13]3[O:12][CH:11]=[C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:27])([F:1])[F:28])[CH:5]=4)[C:14]=3[CH:15]=2)=[N:20][N:21]=1)[CH3:25])(=[O:31])[CH3:30]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 66777355Diethylazodicarboxylate tolueneHCID 68663726(1S)-1-[5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethanol

生成物 1

HCID 68663329(1R)-1-[5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethyl acetate収率 94%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (1S)-1-[5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-yl]ethanol (390 mg, 1.00 mmol), acetic acid (0.114 mL, 2.00 mmol) and triphenylphosphine (394 mg, 1.50 mmol) in tetrahydrofuran (5 mL) was added dropwise 40% diethyl azodicarboxylate-toluene solution (0.653 mL, 1.50 mmol) at 0° C., and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1) to give the title compound (406 mg, yield 94%) as a colorless oil.

後処理

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1)

出典と根拠

ORDレコード
ord-bf932d1d22194f16afe04bd7cdfc4a71
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

関連ノート

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