Pyridine → HCID 15723365, compound

HRID 654957Notes

Reaction equation

HRID 654957 reaction equation
[O:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([Si:26]([CH3:29])([CH3:28])[CH3:27])[O:24][CH:25]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].N1C=CC=C[CH:31]=1.[C:36](=[O:39])(O)[O-:37].[Na+].C(OCC)C>C(OC(=O)C)(=O)C.O>[C:36]([O:37][CH:20]([C:21]1[CH:22]=[C:23]([Si:26]([CH3:27])([CH3:28])[CH3:29])[O:24][CH:25]=1)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:1][Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:4])(=[O:39])[CH3:31]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 53939311HCID 53939311, compound

Product 1

HCID 15723365HCID 15723365, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 4-(12-t-butyldimethylsiloxydodecyl)-2-trimethylsilylfuran (0.46 g, 1.0 mmol) and pyridine (0.3 ml) in acetic anhydride (4 ml) was stirred at 0° under nitrogen for 1/2 hour, then 3.5 hours at room temperature. Approximately 1 ml saturated sodium bicarbonate solution was added to the reaction mixture, which was subsequently poured into ethyl ether and water. The organic portion was washed successively three times with water, once with saturated sodium bicarbonate solution, once with water, once with 10% copper sulfate solution, twice with water, once with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a pale oil. The acetate (20% ethyl ether/hexane) was purified by flash chromatography (silica, 7% ethyl ether/petroleum ether) to give a colorless oil.

Workup

  1. custom3.5 hours
  2. customat room temperature
  3. washThe organic portion was washed successively three times with water
  4. dry with materialonce with saturated sodium bicarbonate solution, once with water, once with 10% copper sulfate solution, twice with water, once with saturated sodium chloride solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a pale oil
  8. customThe acetate (20% ethyl ether/hexane) was purified by flash chromatography (silica, 7% ethyl ether/petroleum ether)
  9. customto give a colorless oil

Sources & evidence

ORD record
ord-6634f552b2c041d9b8367f59edad75d8
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

Loading…