3-Bromo-1-propanol → Phosphoric acid di-tert-butyl ester 3-hydroxy-propyl ester

HRID 585154ノート

反応式

HRID 585154 の反応式
[C:1]([O:5][P:6](=[O:13])([O-:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH2:32][CH2:33][CH2:34][OH:35]>COCCOC>[OH:35][CH2:34][CH2:33][CH2:32][O:13][P:6](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 123083-Bromo-1-propanolHCID 22339116Tetra-n-butylammonium di-tert-butylphosphate

生成物 1

HCID 85869323Phosphoric acid di-tert-butyl ester 3-hydroxy-propyl ester収率 100%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a 100 mL flask was added tetra-n-butyl ammonium phosphoric acid di-tert-butyl ester salt (3.08 g, 6.8 mmol), ethylene glycol dimethyl ether (10 mL), and 3-bromo-1-propanol (freshly distilled from potassium carbonate). The reaction mixture was heated to reflux for 2.5 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl ether (60 mL) and cooled in a refrigerator until a white solid precipitated. The solid was filtered through Celite and the filtrate was evaporated in vacuo, affording the title compound as a clear oil (1.85 g, ˜100%). 1H NMR (CDCl3, 500 MHz) δ 4.10 (m, 2H), 3.73 (m, 2H), 1.84 (m, 2H), 1.46 (s, 18H).

後処理

  1. distillationfreshly distilled from potassium carbonate)
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 2.5 hours
  4. additionthe reaction mixture was diluted with ethyl ether (60 mL)
  5. temperaturecooled in a refrigerator until a white solid
  6. customprecipitated
  7. filtrationThe solid was filtered through Celite
  8. customthe filtrate was evaporated in vacuo

出典と根拠

ORDレコード
ord-eb764b8c137c4d0db462103c93857ca7
出典データセット
uspto-grants-2005_08
特許番号
US06930100B2

反応ノート

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