Pyridine → Trimethylsilyl crotonate

HRID 714581Notes

Reaction equation

HRID 714581 reaction equation
[C:1]([OH:6])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH3:7][Si:8]([CH3:11])([CH3:10])Cl.N1C=CC=CC=1>C(OCC)C>[C:1]([O:6][Si:8]([CH3:11])([CH3:10])[CH3:7])(=[O:5])/[CH:2]=[CH:3]/[CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 637090Crotonic Acid

Product 1

HCID 5702560Trimethylsilyl crotonateYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
38 °C

Procedure

To a single-neck reaction flask (250 mL) were added of crotonic acid (10.750 g, 0.125 mol), anhydrous ethyl ether (125 mL) and trimethyl chlorosilane (19 mL, 0.150 mol). The mixture was stirred for 5 min. Pyridine (12 mL, 0.150 mol) was dropwise added into the resulting mixture under stirring at the temperature of 35° C. After the addition finished, the mixture was warmed up to the temperature of 38° C. and stirred under relux for 3 hr. The white solid was filtered in vacuo. Ethyl ether was evaporated under atmospheric pressure. The resultant was distilled under reduced pressure to collect the fraction under 10 mmHg at the temperature of 46° C.-48° C. to give (E)-trimethylsilyl 2-butenoate as a colorless liquid (12.242 g). Yield: 62.0%.

Workup

  1. stirringunder stirring at the temperature of 35° C
  2. additionAfter the addition
  3. stirringstirred under relux for 3 hr
  4. filtrationThe white solid was filtered in vacuo
  5. customEthyl ether was evaporated under atmospheric pressure
  6. distillationThe resultant was distilled under reduced pressure
  7. customto collect the fraction under 10 mmHg at the temperature of 46° C.-48° C.

Sources & evidence

ORD record
ord-d93b544677664a049491f249d7e69701
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Reaction notes

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