Ethyl Acetate → (R)-5-(4-{1-ethyl-1-[3'-(1-ethyl-1-trimethylsilanyloxy-propyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one

HRID 546830ノート

反応式

HRID 546830 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([C:14]([CH2:22][CH3:23])([O:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=1.[CH2:24]([C:26]([C:45]1[CH:58]=[CH:57][C:48]([O:49][CH2:50][C@@H:51]2[O:55][C:54](=[O:56])[CH2:53][CH2:52]2)=[C:47]([CH3:59])[CH:46]=1)([C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[C:31]([CH3:44])[CH:30]=1)[CH2:27][CH3:28])[CH3:25].C(OCC)(=O)C>CN(C)C=O>[CH2:24]([C:26]([C:45]1[CH:58]=[CH:57][C:48]([O:49][CH2:50][C@@H:51]2[O:55][C:54](=[O:56])[CH2:53][CH2:52]2)=[C:47]([CH3:59])[CH:46]=1)([C:29]1[CH:34]=[CH:33][C:32]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([CH2:22][CH3:23])([O:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH2:15][CH3:16])[CH:9]=2)=[C:31]([CH3:44])[CH:30]=1)[CH2:27][CH3:28])[CH3:25]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 57708911(R)-5-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-oneHCID 57709150[1-(3-Bromo-phenyl)-1-ethyl-propoxy]-trimethyl-silane

生成物 1

HCID 57709099(R)-5-(4-{1-ethyl-1-[3'-(1-ethyl-1-trimethylsilanyloxy-propyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one収率 49.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (1.49 mg, 0.002 mmol), a 2 M sodium carbonate solution (0.1 mL, 0.2 mmol) and [1-(3-bromo-phenyl)-1-ethyl-propoxy]-trimethyl-silane (Example 17-(1); 26.25 mg, 0.091 mmol) were added to a solution of (R)-5-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one (Example 15-(3); 30 mg, 0.061 mmol) in N,N-dimethylformamide (0.1 mL) at room temperature, and the mixture was stirred at 85° C. for 13.5 hours. Ethyl acetate was added to the reaction solution. The organic layer was washed with distilled water and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1, developed twice) to give the title compound (18 mg, 49.2%).

後処理

  1. washThe organic layer was washed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1

出典と根拠

ORDレコード
ord-f00003db933f489a890156e8905ea60c
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

読み込み中…