Pyridine → HCID 22116725, compound

HRID 1460286Notes

Reaction equation

HRID 1460286 reaction equation
[CH3:1][Si:2]([CH3:25])([CH3:24])[O:3][Si:4]([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.N1C=CC=CC=1.Cl[C:33]([O:35][CH:36]=[CH2:37])=[O:34]>CCOCC>[CH:36]([O:35][C:33]([N:11]1[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][CH2:5][Si:4]([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[O:3][Si:2]([CH3:24])([CH3:1])[CH3:25])[CH2:9][CH2:10]1)=[O:34])=[CH2:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 78808Vinyl chloroformateHCID 22116734HCID 22116734, compound

Product 1

HCID 22116725HCID 22116725, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 250 mL 3-neck round bottom flask fitted with a magnetic stirrer, condenser, nitrogen blanket, dropping funnel, thermometer and ice-water bath was added 5.0 g (11.8 mmol) of 3-tris(trimethylsiloxy)silylpropyl piperazine, 0.98 g (12.4 mmol) pyridine and 100 mL ether. To the reaction mixture was added 1.32 g (12.4 mmol) vinyl chloroformate so that the temperature remained below 15°. After stirring for 18 hours the reaction mixture was washed with 100 mL 2N HCl, 100 mL 2N NaOH and the organic phase was dried over magnesium sulfate. The solvent was removed on a rotary evaporator and the resulting oil was chromatographed (silica gel, methylene chloride). The product was recovered as an oil 4.0 g (8.1 mmol, 68.8% yield). FTIR (neat, capillary) 2957.40, 2900.69, 2808.30, 2770.50, 1646.32, 1460.48, 1429.87, 1373.46, 1353.45, 1334.61, 1291.27, 1249.73, 1227.01, 1187.92, 1152.02, 1100.89, 1039.50, 1000.33, 952.03, 833.45, 752.98, 712.79, 686.52, 656.44. NMR (CDCl3) 6.89-7.30 (1H,dd), 4.28- 4.76 (2H,m), 3.30-3.60 (2H,m), 2.19-2.40 (2H,m), 1.21-1.63 (2H,m), 0.17-0.63 (2H,m), 0.00 (27H,s). ##STR37##

Workup

  1. customTo a 250 mL 3-neck round bottom flask fitted with a magnetic stirrer, condenser
  2. customremained below 15°
  3. washwas washed with 100 mL 2N HCl, 100 mL 2N NaOH
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customThe solvent was removed on a rotary evaporator
  6. customthe resulting oil was chromatographed (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-b8cbd65a144241de9187a4819009dfae
Source dataset
uspto-grants-1991_12
Patent number
US05070215

Reaction notes

Loading…