Triethylamine → Ethyl 4-butyrylbenzoate

HRID 1424242ノート

反応式

HRID 1424242 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 67980577Ethyl 4-butyrylbenzoate

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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 (Intermediate 1). 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).

後処理

  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)

出典と根拠

ORDレコード
ord-f404bb61c109453b9a974f935b5b7e95
出典データセット
uspto-grants-2015_01
特許番号
US08927577B2

反応ノート

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