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 547037Notes

Reaction equation

HRID 547037 reaction equation
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]

Participants

6

Reactant 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

Product 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-pyranYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-e564c01a86404302a06bbf22e4e5ea98
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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