Diisobutylaluminum hydride → 2-(4-Phenylphenoxy)ethanol

HRID 459139ノート

反応式

HRID 459139 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 3029632-(4-Phenylphenoxy)ethanol

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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%

出典と根拠

ORDレコード
ord-2484a88e82574949af538a0e1631053c
出典データセット
uspto-grants-2007_03
特許番号
US07192982B2

反応ノート

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