Pyridine → 3-(2-Trimethylsilyl-4-furyl)propyl dodecanoate

HRID 1090912Notes

Reaction equation

HRID 1090912 reaction equation
N1C=CC=CC=1.[CH3:7][Si:8]([CH3:19])([CH3:18])[C:9]1[O:13][CH:12]=[C:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH:10]=1.[C:20](Cl)(=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1.CCOCC>[C:20]([O:17][CH2:16][CH2:15][CH2:14][C:11]1[CH:10]=[C:9]([Si:8]([CH3:7])([CH3:18])[CH3:19])[O:13][CH:12]=1)(=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8166Dodecanoyl chlorideHCID 150370913-(2-Trimethylsilyl-4-furyl)propan-1-ol

Product 1

HCID 150371273-(2-Trimethylsilyl-4-furyl)propyl dodecanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (0.06 ml, 0.72 mmol) was added to a mixture of 3-(5-trimethylsilyl-3-furyl)propan-1-ol (from above) and lauroyl chloride (0.17 ml, 0.72 mmol) in tetrahydrofuran (4 ml) at room temperature. After 14 hours, the mixture was diluted with ether (10 ml) and washed successively with water, copper (II) sulphate and brine. Evaporation of the dried (magnesium sulphate) organic layers gave an oil, which was purified by preparative TLC (20x20 cm, 500u silica plate; developed with 10% ethyl ether/petroleum ether). The title ester was obtained as a colorless oil.

Workup

  1. washwashed successively with water, copper (II) sulphate and brine
  2. customEvaporation of the
  3. dry with materialdried (magnesium sulphate) organic layers
  4. customgave an oil, which
  5. customwas purified by preparative TLC (20x20 cm, 500u silica plate; developed with 10% ethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-74a6703dab484d6ab198abc6b716cca5
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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