Pyridine → HCID 57708953, compound

HRID 546812Notes

Reaction equation

HRID 546812 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]([Si:20]([CH3:50])([CH3:49])[O:21][CH:22]([C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:36]2[CH:41]=[CH:40][C:39](O)=[C:38]([CH3:43])[CH:37]=2)([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:27][C:26]=1[CH3:44])([CH3:19])([CH3:18])[CH3:17].N1C=CC=CC=1.[Cl-].[NH4+]>ClCCl.CCCCCC.C(OCC)(=O)C>[C:16]([Si:20]([CH3:50])([CH3:49])[O:21][CH:22]([C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:36]2[CH:41]=[CH:40][C:39]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[C:38]([CH3:43])[CH:37]=2)([CH2:32][CH3:33])[CH2:34][CH3:35])=[CH:27][C:26]=1[CH3:44])([CH3:17])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 67749Trifluoromethanesulfonic anhydrideHCID 58598381HCID 58598381, compound

Product 1

HCID 57708953HCID 57708953, compoundYield 755.6%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.51 mL, 3.09 mmol) was added to a solution of 4-(1-{4-[3-(t-Butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenol (Example 3-(4); 1.18 g, 2.38 mmol) in dichloromethane (40 mL) and pyridine (0.35 mL, 4.28 mmol) at room temperature, and the mixture was stirred at the same temperature for 20 minutes. A saturated aqueous ammonium chloride solution, ethyl acetate and hexane were added to the mixture. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only to hexane/ethyl acetate=97/3) to give the title compound (11.31 g, 88%).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane only to hexane/ethyl acetate=97/3)

Sources & evidence

ORD record
ord-0afe1744dcc941a095250d82dd3c739b
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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