Sodium Hydroxide → (4-(Diphenylamino)phenyl)methanol

HRID 1786788

反応式

HRID 1786788 の反応式
[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[OH-].[Na+]>CO.O>[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 4311764Sodium borohydride

生成物 1

HCID 11323339(4-(Diphenylamino)phenyl)methanol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

To a solution of 2B (3.637 g, 13.3 mmol) in methanol was added dropwise at 0° C. a solution of NaBH4 added to 3.9 g NaOH dissolved in 7.8 mL H2O. The solution was allowed to stir at room temperature overnight. Water was added and the product was extracted with ether (2×) and washed with brine (2×). The combined ether extracts were dried over MgSO4. The solvent was removed and the product was purified using flash chromatography with a hexanes and then ethyl acetate. The ethyl acetate fraction was collected and the solvent removed to reveal 2.667 g (74%) of a honey yellow crystal solid. 1H NMR (CDCl3): δ4.63 (d, 2H), δ6.97-7.06 (m, 6H), δ7.09 (m, 2H), δ7.20-7.28 (m, 6H); m/z 298.1 (M++Na), 276.1 (M++H), 258.1 (M+-H2O).

後処理

  1. extractionthe product was extracted with ether (2×)
  2. washwashed with brine (2×)
  3. dry with materialThe combined ether extracts were dried over MgSO4
  4. customThe solvent was removed
  5. customthe product was purified
  6. customThe ethyl acetate fraction was collected
  7. customthe solvent removed

出典と根拠

ORDレコード
ord-d21e6c91ab2540298a5395a1d73bf922
出典データセット
uspto-grants-2009_03
特許番号
US07507840B2

関連ノート

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