Pyridine → 4-(4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenylethynyl)-4-trimethylsilanyloxy-tetrahydro-pyran

HRID 547037노트

반응식

HRID 547037 반응식
N1C=CC=CC=1.[O:7]([Si:15]([CH3:18])([CH3:17])[CH3:16])S(C(F)(F)F)(=O)=O.[CH2:19]([C:21]([C:40]1[CH:45]=[CH:44][C:43]([C:46]#[C:47][C:48]2(O)[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)=[C:42]([CH3:55])[CH:41]=1)([C:24]1[CH:29]=[CH:28][C:27]([B:30]2[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:38])([CH3:37])[O:31]2)=[C:26]([CH3:39])[CH:25]=1)[CH2:22][CH3:23])[CH3:20].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:19]([C:21]([C:40]1[CH:45]=[CH:44][C:43]([C:46]#[C:47][C:48]2([O:7][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)=[C:42]([CH3:55])[CH:41]=1)([C:24]1[CH:29]=[CH:28][C:27]([B:30]2[O:31][C:32]([CH3:37])([CH3:38])[C:33]([CH3:35])([CH3:36])[O:34]2)=[C:26]([CH3:39])[CH:25]=1)[CH2:22][CH3:23])[CH3:20]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 577089554-(4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenylethynyl)-tetrahydro-pyran-4-ol

생성물 1

HCID 577090594-(4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenylethynyl)-4-trimethylsilanyloxy-tetrahydro-pyran수율 87.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Pyridine (0.353 mL, 4.380 mmol) and trimethylsilyl triflate (0.396 mL, 2.189 mmol) were added to a solution of 4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenylethynyl)-tetrahydro-pyran-4-ol (Example 130-(3); 0.55 g, 1.095 mmol) in dichloromethane (10 mL) at 0° C., and the mixture was stirred for 30 minutes. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was 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) to give the target compound as a colorless oil (548 mg, 87%).

후처리

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50)

출처 및 근거

ORD 기록
ord-e564c01a86404302a06bbf22e4e5ea98
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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