Pyridine → HCID 53767758, compound

HRID 1460287Notes

Reaction equation

HRID 1460287 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][Si:8]([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[O:9][Si:10]([CH3:13])([CH3:12])[CH3:11].N1C=CC=CC=1.Cl[C:31]([O:33][CH:34]=[CH2:35])=[O:32]>CCOCC>[C:31](=[O:32])([O:33][CH:34]=[CH2:35])[O:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][Si:8]([O:9][Si:10]([CH3:11])([CH3:12])[CH3:13])([O:19][Si:20]([CH3:22])([CH3:21])[CH3:23])[O:14][Si:15]([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 78808Vinyl chloroformateHCID 22116749HCID 22116749, compound

Product 1

HCID 53767758HCID 53767758, compound

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, ice-water bath and thermometer was added 6.3 g (15.8 mmol) N-(2-hydroxyethyl)-3-aminopropyltris(trimethylsiloxy) silane, 1.37 g (17.4 mmol) of pyridine and 100 mL ether. To the reaction mixture was added 1.68 g (15.8 mmol) of vinyl chloroformate so that the temperature remained below 5° C. After stirring at room temperature for 24 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, 4.3 g, chromatographed (silica gel, ethyl acetate 20% methylene chloride 80%). The oil recovered weighed 2.99 g (6.4 mmol, 25.4% yield). FTIR (neat, capillary) 2957.62, 2899.00, 1720.60, 1702.33, 1648.16, 1470.55, 1420.23, 1373.91, 1291.12, 1249.88, 1196.62, 1152.74, 1039.27, 951.52, 833.44, 753.18, 715.26, 686.53, 658.78. NMR (CDCl 3) 6.85-7.20 (1H,dd), 4.20-4.69 (2H,m), 3.36-3.71 (2H,bd), 3.00-3.36 (4H,m), 1.00-1.65 (2H,m), 0.09-0.40 (2H,m), 0.00 (27H,s). ##STR39##

Workup

  1. customTo a 250 mL 3-neck round bottom flask fitted with a magnetic stirrer, condenser
  2. customremained below 5° C
  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, 4.3 g, chromatographed (silica gel, ethyl acetate 20% methylene chloride 80%)
  7. customThe oil recovered

Sources & evidence

ORD record
ord-985339f7745741acb775c69fce5ed12a
Source dataset
uspto-grants-1991_12
Patent number
US05070215

Reaction notes

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