Diisobutylaluminum hydride → 2-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-2-(3,5-difluorophenyl)ethanol

HRID 602680ノート

反応式

HRID 602680 の反応式
C[O:2][C:3](=O)[C:4](=[C:13]1[CH2:16][N:15]([CH:17]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:14]1)[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[CH:6]=1.CC(C[AlH]CC(C)C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.C1COCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:17]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[N:15]2[CH2:16][C:13](=[C:4]([C:5]3[CH:6]=[C:7]([F:12])[CH:8]=[C:9]([F:11])[CH:10]=3)[CH2:3][OH:2])[CH2:14]2)=[CH:26][CH:27]=1

参加物

6

反応物 3

HCID 14487Diisobutylaluminum hydrideHCID 62649Sodium sulfate decahydrateHCID 57559907Methyl {1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate

生成物 1

HCID 113742342-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-2-(3,5-difluorophenyl)ethanol

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2.11 g (4.45 mmol) of methyl{1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate in 40 mL of hexanes and 40 mL of CH2Cl2 was added a solution of 26.7 mL (26.7 mmol) of DIBAL-H (1M solution in THF followed by stirring for 1 h at −78° C. Then the reaction mixture was warmed to rt for 1.5 h and 8 g of sodium sulfate decahydrate was added to quench the reaction followed by stirring for 1 h at rt. The quenched reaction mixture was filtered and the organic layer concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound as white solid. 1NMR (CDCl3) δ 3.99 (s, 2H), 4.03 (s, 2H), 4.35 (s, 2H), 4.54 (s, 1H), 6.70-6.80 (m, 3H), 7.30-6-7.40 (m, 8H). Mass Spectrum: m/e=446 (M+1 35Cl, 35Cl) and 448 (M+1 35Cl, 37Cl).

後処理

  1. temperatureThen the reaction mixture was warmed to rt for 1.5 h
  2. customto quench the reaction
  3. stirringby stirring for 1 h at rt
  4. customThe quenched reaction mixture
  5. filtrationwas filtered
  6. concentrationthe organic layer concentrated
  7. customThe residue was purified by silica gel chromatography with hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-a88c1ef37c094b7f85ef291d7ef77235
出典データセット
uspto-grants-2011_03
特許番号
US07906503B2

反応ノート

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