Formaldehyde → 4-(1-Triisopropylsilanyl-1H-pyrrol-3-ylmethyl)-morpholine

HRID 241707

反応式

HRID 241707 の反応式
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:7]([Si:10]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)([CH3:9])[CH3:8].[CH2:22]=O.[OH-].[Na+]>C(O)(=O)C.O>[CH:19]([Si:10]([CH:7]([CH3:9])[CH3:8])([CH:16]([CH3:18])[CH3:17])[N:11]1[CH:15]=[CH:14][C:13]([CH2:22][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:12]1)([CH3:21])[CH3:20]

参加物

7

反応物 4

HCID 712FormaldehydeHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 145136N-Triisopropylsilylpyrrole

生成物 1

HCID 666367604-(1-Triisopropylsilanyl-1H-pyrrol-3-ylmethyl)-morpholine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a solution of morpholine (98.5 mmoles) in acetic acid (100 ml) at 0° C. there are added 1-triisopropylsilanyl-1H-pyrrole (89.5 mmoles) and formaldehyde (89.5 mmoles) 37% in water. The reaction mixture is stirred overnight at ambient temperature. The solution is brought to alkaline pH (10-12) using 20% aqueous NaOH solution and is then extracted with DCM. The organic phase is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt) to yield the title product, which is used directly in the next Step.

後処理

  1. extractionis then extracted with DCM
  2. washThe organic phase is washed with water and with saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue obtained
  7. customis purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt)

出典と根拠

ORDレコード
ord-c11e6dbcf27e48709f34fc0e343e6f1e
出典データセット
uspto-grants-2014_02
特許番号
US08653073B2

関連ノート

読み込み中…