1-Butanol → HCID 9926041, compound

HRID 1700820Notes

Reaction equation

HRID 1700820 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:10])[CH:8]=O)(=[O:3])[CH3:2].[C:11]1([S:17]([C:20]#[N:21])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.B(OCCCC)(OCCCC)OCCCC.C(O)CCC>>[C:1]([O:4][C:5]1[C:20]([S:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)(=[O:19])=[O:18])=[N:21][CH:8]=[C:7]([CH3:10])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 12712Tributyl borateHCID 846993-Formylbut-2-enyl acetateHCID 10313279Benzenesulfonyl cyanide

Product 1

HCID 9926041HCID 9926041, compoundYield 24%

Conditions

Temperature
108 °C

Procedure

First, 5.0 g (39.6 mmol) of 4-acetoxy-2-methyl-2-butenal, 7.05 g (39.6 mmol) of benzenesulfonyl cyanide, 0.91 g (4.0 mmol) of tributyl borate and 1-butanol (0.59 g, 7.9 mmol) were introduced to a 3-necked flask (100 ml volume) equipped with a thermometer, a magnetic stirrer, a Dean-Stark water type distilling receiver and a condenser tube. Toluene (20 ml) was added as the solvent. Then the mixture was heated under reflux for 22 hours while agitating at an internal temperature of 108° C. in a nitrogen atmosphere, separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure to give the desired, crude product. The crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/3) to give 2.62 g of 3-acetoxy-2-benzenesulfonyl-5-methylpyridine with the following properties as a brown, oily substance (yield of 24% based on benzenesulfonyl cyanide).

Workup

  1. customequipped with a thermometer, a magnetic stirrer
  2. distillationa Dean-Stark water type distilling receiver and a condenser tube
  3. additionToluene (20 ml) was added as the solvent
  4. temperatureThen the mixture was heated
  5. temperatureunder reflux for 22 hours
  6. customseparating
  7. customremoving water that
  8. customwas produced
  9. temperatureAfter this solution was cooled to room temperature
  10. customthe low-boiling components, such as solvent, etc., were removed under reduced pressure
  11. customto give the
  12. customThe crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-a22f372162ae4acebfbdcff57d1ea721
Source dataset
uspto-grants-2002_02
Patent number
US06350876B2

Reaction notes

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