Acetic Acid → 2-[(Benzylamino)methyl]-5-tert-butylphenol

HRID 1173297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173297
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][C:5]=1[OH:14].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl.CO>[CH2:15]([NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:11])([CH3:13])[CH3:12])=[CH:6][C:5]=1[OH:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 98157872-Aminomethyl-5-tert-butylphenol hydrochloride

Produkt 1

HCID 687149132-[(Benzylamino)methyl]-5-tert-butylphenol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 0.216 g (1.0 mmol) of the product of Example 1 and 0.108 g (0.1 mmol) of benzaldehyde suspended in 5 mL of 1,2-dichloroethane was added 0.5 mL acetic acid and 1 g of finely powdered 4 Å molecular sieves. The reaction mixture was stirred under a nitrogen atmosphere at room temperature overnight, then 1.12 g (5 mmol) of sodium triacetoxyborohydride was added. The reaction was then stirred an addition day at room temperature, then diluted with CH2Cl2 and MeOH. The mixture was filtered through a pad of Celite filter aid eluted with CH2Cl2, and the filtrate was washed with saturated aq. NaHCO3. The organic layer was the separated, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a flash chromatography column eluted with CH2Cl2-MeOH—NH4HO (97:2:1) to afford the title compound.

Aufarbeitung

  1. stirringThe reaction was then stirred
  2. additionan addition day at room temperature
  3. filtrationThe mixture was filtered through a pad of Celite
  4. filtrationfilter aid
  5. washeluted with CH2Cl2
  6. washthe filtrate was washed with saturated aq. NaHCO3
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified on a flash chromatography column
  11. washeluted with CH2Cl2-MeOH—NH4HO (97:2:1)

Quellen und Nachweise

ORD-Eintrag
ord-4d7fadf2f97546d9a0502766b6d2115c
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834062B2

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