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

HRID 1662331ノート

反応式

HRID 1662331 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][CH3:22])[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][CH3:22])[CH:16]=1)([CH3:1])[CH3:3]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705757Methyl 2-(1,1-dimethylethyl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylate

生成物 1

HCID 57706653(2-(1,1-Dimethylethyl)-3'-(methyloxy)-1,1'-biphenyl-4-yl)methanol収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled solution of 12.1 (1.01 g, 3.38 mmol) in dry THF (10.0 mL) at 0° C., was added LAH (1.0 M solution in THF (6.7 mL, 6.7 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), 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 12.2 as a colorless oil (0.82, 90%). 1H NMR (500 MHz, CDCl3) δ ppm 7.56 (1H, s), 7.29 (1H, t, J=3.8 Hz), 7.24 (1H, m), 7.07 (1H, d, J=7.6 Hz), 6.93 (2H, m), 6.86 (1H, d, J=1.5 Hz), 4.77 (2H, s), 3.85 (3H, s), 1.72 (1H, s), 1.26 (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 materialdried 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-936b59f5844b49b68ea89bb81b2186ef
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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