Sodium hydride → HCID 68680479、化合物

HRID 1454563ノート

反応式

HRID 1454563 の反応式
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][NH:14][C:13]1=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:20][O:21][CH:22]([O:26][CH3:27])[CH2:23][CH2:24]Br>CC(N(C)C)=O.C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][N:14]([CH2:24][CH2:23][CH:22]([O:26][CH3:27])[O:21][CH3:20])[C:13]1=[O:17])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 57530581HCID 57530581、化合物

生成物 1

HCID 68680479HCID 68680479、化合物収率 100.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 31374Dimethylacetamide溶媒2 回

実験手順

1-[3-(tert-Butyldimethylsilanyloxy)propyl]imidazolidin-2-one (17.65 g, 68.30 mmol; prepared as described in Preparation 1) was slowly added to a suspension of NaH (8.20 g, 204.9 mmol, 3.0 eq, 40% mineral oil) in DMA (400 mL). Deprotonation was monitored with a bubbler, and bubbling was ceased after one hour of stirring at room temperature. A solution of 3-bromopropionaldehyde dimethyl acetal (25.0 g, 136.6 mmol, 2.0 eq) in DMA (100 mL) was slowly added to the reaction mixture over a period of 2 hours via an addition funnel. Following an additional hour of stirring at room temperature, the solution was concentrated in vacuo and the crude reaction mixture was taken up in DCM (200 mL) and washed with water (2×200 mL) and brine (2×200 mL). The organic phase was dried over Na2SO4, filtered and concentrated to afford the title compound (24.53 g, 68.8 mmol) as light yellow oil. The material was used without further purification.

後処理

  1. custombubbling
  2. waitFollowing an additional hour
  3. stirringof stirring at room temperature
  4. concentrationthe solution was concentrated in vacuo
  5. customthe crude reaction mixture
  6. washwashed with water (2×200 mL) and brine (2×200 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-11a55a5c716d42ee83cf3143da11b0cd
出典データセット
uspto-grants-2009_01
特許番号
US07479562B2

反応ノート

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