Tetrahydrofuran → Methyl 4-(2-hydroxyethyl)benzoate

HRID 1828005노트

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HRID 1828005 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[CH:6][CH:5]=1.B1C2CCCC1CCC2.[O:22]1CCCC1>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:22])=[CH:6][CH:5]=1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 583124Methyl 4-ethenylbenzoate

생성물 1

HCID 14078904Methyl 4-(2-hydroxyethyl)benzoate수율 64.7%

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온도
0 °C

실험 절차

Methyl-4-vinylbenzoate 70 (2.270 g, 14.00 mmol) was dissolved in 50 ml of tetrahydrofuran and cooled to 0° C. 9-BBN (0.5M in THF)(28.00 ml, 14.00 mmol) was added and the mixture was stirred for 2 hours. The solution was allowed to warm to room temperature and stirred for an additional 2 hours. The reaction was cooled to 0° C. and quenched with alkaline hydrogen peroxide. The mixture was then extracted with diethyl ether. The extracts were dried over anhydrous sodium sulfate and concentrated en vacuo. The residue was purified by flash chromatography on silica eluted with 4:1 hexane/acetone to give 1.632g (64.7%) of 4-(2-hydroxyethyl)benzoic acid methyl ester 71 as a clear oil.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for an additional 2 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with alkaline hydrogen peroxide
  5. extractionThe mixture was then extracted with diethyl ether
  6. dry with materialThe extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated en vacuo
  8. customThe residue was purified by flash chromatography on silica
  9. washeluted with 4:1 hexane/acetone

출처 및 근거

ORD 기록
ord-ea1f177ee5ea46778e504a90ed658dd7
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07056903B2

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