Acetic Anhydride → N-(4-benzyloxybenzyl)acetohydroxamic acid

HRID 649240

반응식

HRID 649240 반응식
C([BH3-])#N.[Na+].[CH2:5]([O:12][C:13]1[CH:21]=[CH:20][C:16]([CH:17]=[N:18][OH:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.CO.C(OCC)(=O)C.O>[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]([C:22](=[O:24])[CH3:23])[OH:19])=[CH:20][CH:21]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

9

반응물 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 7633594-Benzyloxy-benzaldehyde oximeHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 129265N-(4-benzyloxybenzyl)acetohydroxamic acid

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium cyanoborohydride (21.3 g) was added in portions to a solution of 4-benzyloxybenzaldehyde oxime (51 g) in acetic acid (250 ml) at ca 50° (cooling). After the reduction was complete, acetic anhydride (22.5 ml) was added in one portion, and the mixture was stirred for 1 hour. The mixture was then poured into water, and the neutral product was isolated with ethyl acetate. The residue was treated with potassium carbonate (2 g) in methanol (400 ml) to hydrolyse the O-acetyl material, then the solvent was evaporated. Addition of 20% citric acid solution (400 ml) and isolation with ethyl acetate furnished N-(4-Benzyloxybenzyl) acetohydroxamic acid (32 g), m.pt. 119°-120° [from ethyl acetate-light petroleum (b.pt. 60°-80°)].

후처리

  1. temperature(cooling)
  2. customthe solvent was evaporated
  3. additionAddition of 20% citric acid solution (400 ml) and isolation with ethyl acetate

출처 및 근거

ORD 기록
ord-e9012f28c19b4f329d9f1a812830a183
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04738986

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