Formaldehyde → HCID 58287018, 화합물

HRID 390074노트

반응식

HRID 390074 반응식
Cl.[CH2:2]([NH:9][OH:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11]([O-:14])(=O)[CH3:12].[Na+].C=O.C(O)/[CH:19]=[CH:20]\[CH2:21][OH:22]>C(O)C>[CH2:2]([N:9]1[CH2:19][CH:20]([CH2:21][OH:22])[CH:12]([CH2:11][OH:14])[O:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 6437902-Butene-1,4-diol, (2Z)-HCID 11332622N-benzylhydroxylamine hydrochloride

생성물 1

HCID 58287018HCID 58287018, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of N-benzylhydroxylamine hydrochloride (13.59 g, 85.15 mmol) and sodium acetate (9.31 g, 114 mmol) were stirred together in ethanol (75 mL) at rt for 15 mins. Aqueous 37% formaldehyde solution (12.68 ml, 170 mmol) was added and stirring continued for 30 mins, then cis-2-butene-1,4-diol (4.67 ml, 56.8 mmol) added and the mixture heated under reflux for 16 h. The solvent was evaporated and the residue dissolved in CHCl3 and washed with aq. sat. NaHCO3, dried (MgSO4) and the solvent evaporated to give a brown syrup suitable for use without further purification (12.5 g, 98%). An aliquot was purified by chromatography on silica gel (EtOAc then EtOAc-MeOH, 95:5) to give ((4RS,5RS)-2-benzylisoxazolidine-4,5-diyl)dimethanol as a colourless syrup. 13C NMR (CDCl3, referenced to the centre line of CDCl3 at 77.0 ppm) δ 136.5, 129.0, 128.4, 127.6, 78.5, 62.4, 61.3, 60.4, 56.8, 45.8.

후처리

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 16 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in CHCl3
  5. washwashed with aq. sat. NaHCO3
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated
  8. customto give a brown syrup suitable for use
  9. customwithout further purification (12.5 g, 98%)
  10. customAn aliquot was purified by chromatography on silica gel (EtOAc

출처 및 근거

ORD 기록
ord-2058c9d0dac74ba0850c74aac57b7a05
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383636B2

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