Triethylamine → Ethyl 4-butyrylbenzoate

HRID 1520797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520797
[OH:1][CH:2]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].C(N(CC)CC)C>ClCCl.CS(C)=O>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][CH:16]=1)(=[O:1])[CH2:3][CH2:4][CH3:5]

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 67981039Ethyl 4-(1-hydroxybutyl)benzoate

Produkt 1

HCID 67980577Ethyl 4-butyrylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of the crude alcohol (1.0 g, 4.5 mmol) in dichloromethane (16.7 mL), dimethylsulfoxide (4.79 mL) and triethylamine (2.28 g, 22.5 mmol) was cooled to 0° C. Sulfur trioxide pyridine complex (2.15 g, 13.5 mmol) was added in portions and the mixture stirred at 0° C. for 1 hour. The reaction was then allowed to warm to room temperature and stir for 2 hours. The reaction was quenched with brine and diluted with dichloromethane. The layers were separated and the aqueous was extracted again with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-30% ethyl acetate in heptane) gave ethyl 4-butyrylbenzoate. 1H NMR (400 MHz, CDCl3, δ): 8.05-8.17 (m, 2H), 8.04-7.92 (m, 2H), 4.40 (q, J=7.15 Hz, 2H), 2.96 (t, J=7.22 Hz, 2H), 1.86-1.69 (m, 2H), 1.40 (t, J=7.12 Hz, 3H), 1.00 (t, J=7.22 Hz, 3H).

Aufarbeitung

  1. additionSulfur trioxide pyridine complex (2.15 g, 13.5 mmol) was added in portions
  2. temperatureto warm to room temperature
  3. stirringstir for 2 hours
  4. customThe reaction was quenched with brine
  5. additiondiluted with dichloromethane
  6. customThe layers were separated
  7. extractionthe aqueous was extracted again with dichloromethane
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by column chromatography (0-30% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-9d5393d78eec4f6895285b8ed6ace1eb
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073871B2

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