Sodium Hydroxide → (2-(1,1-Dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl-4-yl)methanol

HRID 1662350ノート

反応式

HRID 1662350 の反応式
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11](OC)=[O:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH3:23])[CH:16]=1)([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH3:23])[CH:16]=1)([CH3:1])[CH3:3]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57706553Methyl 2-(1,1-dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl-4-carboxylate

生成物 1

HCID 57705661(2-(1,1-Dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl-4-yl)methanol収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled solution of 41.1 (0.87 g, 2.79 mmol) in dry THF (10.0 mL) at 0° C., was added LAH (1.0 M solution in THF (5.5 mL, 5.5 mmol)). Upon complete addition, the reaction was allowed to warm to room temperature and monitored by TLC and LCMS. Upon completion, 1N NaOH (5 mL) was carefully added to quench the reaction. The resulting solution was extracted with EtOAc (3×10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-40% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 41.2 as a colorless oil (0.72, 91%). 1H NMR (500 MHz, CDCl3) δ ppm 7.53 (1H, d, J=1.5 Hz), 7.26 (1H, m), 7.19 (1H, dd, J=7.7, 1.8 Hz), 7.04 (1H, d, J=7.6 Hz), 6.89 (3H, m), 4.74 (2H, d, J=3.2 Hz), 4.08 (2H, m), 1.71 (1H, s), 1.42 (3H, t, J=7.0 Hz), 1.23 (9H, s).

後処理

  1. additionUpon complete addition
  2. customto quench
  3. customthe reaction
  4. extractionThe resulting solution was extracted with EtOAc (3×10 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-40% EtOAc in hexanes)
  9. additionFractions containing the desired product
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-03b6355edbe04b338c1f48d79fa2b2d8
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

読み込み中…