Tetraethylammonium tetrahydroborate → Methyl 2-(2-hydroxypropan-2-yl)-6-(4-methylphenyl)pyridine-4-carboxylate

HRID 1909128ノート

反応式

HRID 1909128 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:10]([C:18]([CH3:20])=[CH2:19])[N:9]=2)=[CH:4][CH:3]=1.[BH4-].C([N+](CC)(CC)CC)C.C([O-])(O)=[O:32].[Na+]>CO.COCCOC.O>[OH:32][C:18]([C:10]1[CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=1)([CH3:20])[CH3:19]

参加物

7

反応物 3

HCID 28251Tetraethylammonium tetrahydroborateHCID 516892Sodium BicarbonateHCID 67339741Methyl 2-(4-methylphenyl)-6-(prop-1-en-2-yl)pyridine-4-carboxylate

生成物 1

HCID 67339432Methyl 2-(2-hydroxypropan-2-yl)-6-(4-methylphenyl)pyridine-4-carboxylate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of methyl 2-(4-methylphenyl)-6-(prop-1-en-2-yl)pyridine-4-carboxylate (191 mg, 0.71 mmol) in methanol (3.6 mL) and DME (3.6 mL) was added cobalt(II)mesotetraphenylporphine (2.4 mg, 3.6 mop. After 30 min, tetraethylammonium borohydride (170 mg, 1.17 mmol) was added in 3 portions over 1 h. Saturated aqueous NaHCO3 was added. The mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 90% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (165 mg). MS 286.1 (M+1).

後処理

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by reverse phase chromatography (C-18, 90% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-3240b01d78964a7f9c81768f8054afd4
出典データセット
uspto-grants-2013_12
特許番号
US08598209B2

反応ノート

読み込み中…