Aluminium lithium hydride → 2,2-Bis(hexyloxy)propan-1-ol

HRID 1518170ノート

反応式

HRID 1518170 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:13][C:14]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH3:24])[C:15](OCCCCCC)=[O:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>CCOCC>[CH2:26]([O:25][C:14]([O:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])([CH3:24])[CH2:15][OH:16])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 46945489Hexyl 2,2-bis(hexyloxy)propanoate

生成物 1

HCID 469453022,2-Bis(hexyloxy)propan-1-ol収率 96.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of LiAlH4 (3.44 g, 90.5 mmol) in Et2O (200 mL) is added a solution of ester 3 (29.5 g, 82.3 mmol) in Et2O (100 mL). After addition, the mixture is refluxed for 6 hours. The reaction mixture is cooled to 0° C. and quenched with ethyl acetate (20 mL) and H2O (20 mL). The mixture is added to saturated potassium sodium tartrate (300 mL) and stirred at 23° C. for 12 hours. The mixture is extracted with Et2O (2×200 mL) and the combined organic layers are dried over anhydrous sodium sulfate. The solvent is removed and the residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane) to give 2,2-bis(hexyloxy)propan-1-ol 4 (20.6 g, 94%) as a colorless oil: Rf (15% EtOAc/hexane)=0.20; IR (thin film, cm−1) 3430, 2955, 2929, 2859, 1467, 1378, 1244, 1155, 1112, 1064, 876; 1H NMR (600 MHz, C6D6) δ 3.58 (d, J=6.6 Hz, 2H), 3.43 (t, J=6.6 Hz, 4H), 1.58 (t, J=6.6 Hz, 1H), 1.53 (m, 4H), 1.36 (s, 3H), 1.34-1.22 (m, 12H), 0.88 (t, J=7.2 Hz, 6H); 13C NMR (150 MHz, C6D6) δ 101.0, 66.2, 61.3, 32.5, 30.9, 26.8, 23.4, 21.3, 14.6.

後処理

  1. additionAfter addition
  2. temperaturethe mixture is refluxed for 6 hours
  3. customquenched with ethyl acetate (20 mL) and H2O (20 mL)
  4. additionThe mixture is added to saturated potassium sodium tartrate (300 mL)
  5. extractionThe mixture is extracted with Et2O (2×200 mL)
  6. dry with materialthe combined organic layers are dried over anhydrous sodium sulfate
  7. customThe solvent is removed
  8. customthe residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-e11bc10098b34d06b3899eed5fcfb5e0
出典データセット
uspto-grants-2012_07
特許番号
US08232423B2

反応ノート

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