Diisobutylaluminum hydride → 2-(4-Phenylphenoxy)ethanol

HRID 459139노트

반응식

HRID 459139 반응식
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:10]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 765876Ethyl (biphenyl-4-yloxy)acetate

생성물 1

HCID 3029632-(4-Phenylphenoxy)ethanol

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of (Biphenyl-4-yloxy)-acetic acid ethyl ester (0.63 g, 2.46 mmol) in dry toluene (15 mL) at −78° C. was added DIBAL-H 1M in toluene (4.92 mL, 4.92 mmol). The solution was stirred at −78° C. for 1 hour, warmed to room temperature and quenched with mixture of a solution of sodium tartrate in water and ethyl acetate for 1 hour. The layers were separated and the aqueous phase further extracted with ethyl acetate. The combined organic layers were dried (MgSO4), concentrated under vacuum and the residue purified bu column chromatography (silica gel, hexanes/Ethyl acetate 4:1, Rf0.1), 48%. 1H-NMR (CDCl3, 200.15 MHz): 7.58–7.26 (m, 8H); 7.00 (d, 2H, J=8.6), 4.14 (t, 2H, J=4.6), 4.02–3.98 (m, 2H); 2.04 (t, 1H, J=5.4).

후처리

  1. temperaturewarmed to room temperature
  2. customquenched with mixture of a solution of sodium tartrate in water and ethyl acetate for 1 hour
  3. customThe layers were separated
  4. extractionthe aqueous phase further extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customthe residue purified bu column chromatography (silica gel, hexanes/Ethyl acetate 4:1, Rf0.1), 48%

출처 및 근거

ORD 기록
ord-2484a88e82574949af538a0e1631053c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192982B2

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