Pyridine → HCID 18426508, compound

HRID 1281044Notes

Reaction equation

HRID 1281044 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][OH:7])(=[O:4])=[O:3].[C:8](=[O:11])([O-])[O-].[Na+].[Na+].N1C=CC=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[C:8]([O:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:11])[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 848342-(Methylsulfonyl)ethanol

Product 1

HCID 18426508HCID 18426508, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Fifty grams 2-(methylsulfonyl)ethanol, 500 mg BHT, 25.61 g sodium carbonate, 0.5 mL pyridine, and 200 mL toluene were combined in a dry 500 mL 3-neck round bottom flask. The flask was outfitted with a mechanical stirrer, a disposable pipet to act as a sparge tube, and addition funnel. Oxygen was bubbled into the solution via the pipet for 30 minutes, and then slowed to a bubble every few seconds. The flask was cooled in an ice-water bath and the pipet pulled out to bring the tip above the solution surface. Fifty ml toluene and 40.1 g acryloyl chloride was added to the addition funnel. The acryloyl chloride solution was added dropwise over 90 minutes. The reaction was stirred at room temperature for two hours, and then heated to 50° C. for one hour. IR(neat): 3107, 3013, 2964, 2933, 1725, 1635, 1461, 1408, 1295, 1186, 1130, 1073, 984, 965, 809, 665, 482, 451 cm−1. 1H NMR (300 Mhz, CDCl3): δ66.40 (d), 6.10 (dd), 5.90 (d), 4.55 (t), 3.35 (t), 2.95 (s). 13C NMR (75.6 Mhz, CDCl3): δ165, 132, 127, 58, 53, 43.

Workup

  1. customThe flask was outfitted with a mechanical stirrer
  2. additiona disposable pipet to act as a sparge tube, and addition funnel
  3. customOxygen was bubbled into the solution via the pipet for 30 minutes
  4. customa bubble every few seconds
  5. temperatureThe flask was cooled in an ice-water bath
  6. additionFifty ml toluene and 40.1 g acryloyl chloride was added to the addition funnel
  7. additionThe acryloyl chloride solution was added dropwise over 90 minutes
  8. temperatureheated to 50° C. for one hour

Sources & evidence

ORD record
ord-291dedf3989743129b296c62748d2b79
Source dataset
uspto-grants-2002_09
Patent number
US06451947B1

Reaction notes

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