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

HRID 1786788

반응식

HRID 1786788 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 11323339(4-(Diphenylamino)phenyl)methanol

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d21e6c91ab2540298a5395a1d73bf922
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507840B2

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