Pyridine → HCID 15723364, compound

HRID 654950Notes

Reaction equation

HRID 654950 reaction equation
[OH:1][CH:2]([C:19]1[CH:20]=[C:21]([Si:24]([CH3:27])([CH3:26])[CH3:25])[O:22][CH:23]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[C:28](OC(=O)C)(=[O:30])[CH3:29].N1C=CC=CC=1>>[C:28]([O:1][CH:2]([C:19]1[CH:20]=[C:21]([Si:24]([CH3:26])([CH3:25])[CH3:27])[O:22][CH:23]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])(=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54310569HCID 54310569, compound

Product 1

HCID 15723364HCID 15723364, compound

Procedure

A solution of 4-(1-hydroxy-9-t-butyldimethylsiloxynonyl)-2-trimethylsilylfuran (0.892 g, 2.17 mmol), acetic anhydride (5 ml) and pyridine (0.729 g, 8.66 mmol) was stirred at room temperature until no starting material was visible by TLC. The reaction mixture was concentrated and the residue was taken up in ethyl ether, washed with 10% hydrochloric acid, saturated sodium bicarbonate, aqueous 5% cupric sulfate solution, water, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give the title compound which was carried on without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with 10% hydrochloric acid, saturated sodium bicarbonate, aqueous 5% cupric sulfate solution, water, saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcc7b3ad520a437f8223d14ad63e0f44
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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