Formaldehyde → HCID 58287018、化合物

HRID 390074ノート

反応式

HRID 390074 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 58287018HCID 58287018、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2058c9d0dac74ba0850c74aac57b7a05
出典データセット
uspto-grants-2013_02
特許番号
US08383636B2

反応ノート

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