4-hydroxy-N-methoxy-N-methyl-3-(morpholinomethyl)benzamide → 4-Hydroxy-3-morpholin-4-ylmethyl-benzaldehyde

HRID 2390548ノート

反応式

HRID 2390548 の反応式
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][C:3]=1[CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C1COCC1.[H-].[Cl-].C1([Zr+2]C2C=CC=C2)C=CC=C1>[OH:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

参加物

4

反応物 1

HCID 866390694-hydroxy-N-methoxy-N-methyl-3-(morpholinomethyl)benzamide

生成物 1

HCID 4373904-Hydroxy-3-morpholin-4-ylmethyl-benzaldehyde

試薬・触媒・溶媒 2

HCID 178420592HCID 178420592、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Bis(cyclopentadienyl)zirconium chloride hydride (4.29 g, 16.27 mmol) was added portionwise over 10 min to a solution of 4-hydroxy-N-methoxy-N-methyl-3-(morpholinomethyl)benzamide (3.8 g, 13.56 mmol) in THF (50 mL), under N2 whilst maintaining the temperature below 20° C. Stirred for 2 h, quenched with saturated potassium sodium tartrate, extracted with EtOAc (3×100 mL), washed with more saturated potassium sodium tartrate and brine, dried (Na2SO4), filtered and evaporated in vacuo. Purified by flash chromatography with EtOAc as eluent to give the sub-title compound as a colourless oil. Yield: 2.1 g

後処理

  1. temperaturewhilst maintaining the temperature below 20° C
  2. customquenched with saturated potassium sodium tartrate
  3. extractionextracted with EtOAc (3×100 mL)
  4. washwashed with more saturated potassium sodium tartrate and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurified by flash chromatography with EtOAc as eluent

出典と根拠

ORDレコード
ord-4d9c20ca0bab46909bf0b805aa674565
出典データセット
uspto-grants-2012_09
特許番号
US08273774B2

反応ノート

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