Acetic Acid → HCID 67165213, Verbindung

HRID 553315

Reaktionsgleichung

Reaktionsgleichung von HRID 553315
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[CH3:10][O:11][C:12](=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CN1CCCC1=O>[CH3:10][O:11][C:12](=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[OH:1])[CH:15]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 702672-(Aminomethyl)phenolHCID 5049666Sodium triacetoxyborohydrideHCID 11819590Methyl 2-(3-formylphenyl)acetate

Produkt 1

HCID 67165213HCID 67165213, VerbindungAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxybenzylamine (407 mg) and (3-formylphenyl)acetic acid methyl ester (594 mg) in dichloromethane (10 mL) and 1-methyl-2-pyrrolidone (10 mL) was treated with acetic acid (333 mg) followed by sodium triacetoxyborohydride (1.41 g) and the whole stirred at room temperature for 18 hours. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, the organic layer was washed twice with saturated aqueous brine before being separated, dried and evaporated under reduced pressure to yield the sub-titled compound (0.81 g).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. washthe organic layer was washed twice with saturated aqueous brine
  3. custombefore being separated
  4. customdried
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-df1025b55b0e4d2da714fab1ad342103
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951954B2

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