Triethylamine → Ethyl 4-butyrylbenzoate

HRID 537425노트

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HRID 537425 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 67980577Ethyl 4-butyrylbenzoate

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-43ffc5ad8ba246ec84a63e15e88e1ba2
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859591B2

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