Potassium Carbonate → 1-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one

HRID 547067ノート

反応式

HRID 547067 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]([C:11]([CH2:13]Cl)=[O:12])([CH3:10])[CH3:9].[CH2:15]([C:17]([C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH3:42])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([B:26]2[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]2)=[CH:22][CH:21]=1)[CH2:18][CH3:19])[CH3:16].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:15]([C:17]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:13][C:11](=[O:12])[C:8]([CH3:10])([CH3:9])[CH3:7])=[C:37]([CH3:42])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([B:26]2[O:27][C:28]([CH3:33])([CH3:34])[C:29]([CH3:31])([CH3:32])[O:30]2)=[CH:22][CH:21]=1)[CH2:18][CH3:19])[CH3:16]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 835721-ChloropinacoloneHCID 516892Sodium BicarbonateHCID 574435234-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol

生成物 1

HCID 574435241-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one収率 32%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

Potassium carbonate (54.5 mg, 0.395 mmol) and 1-chloropinacolin (71 mg, 0.526 mmol) were added to a solution of 4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol (Example 143-(3); 100 mg, 0.263 mmol) in N,N-dimethylformamide (2 mL), and the mixture was stirred with microwave heating at 140° C. for 15 minutes. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50, 40 minutes) to give the target compound as a colorless oil (39.7 mg, 32%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50, 40 minutes)

出典と根拠

ORDレコード
ord-b1b2032ffc654c0f97465a4e91084aa7
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

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