Sodium hydride → Ethyl trans-3, 5-di-t-butylcinnamate

HRID 964928

反応式

HRID 964928 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[Na].[CH3:18][CH2:19][O:20][C:21]([CH2:23]P(OCC)(OCC)=O)=[O:22].[H-].[Na+]>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)/[CH:8]=[CH:23]/[C:21]([O:20][CH2:19][CH3:18])=[O:22])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 12682533,5-Bis(tert-butyl)benzaldehydeHCID 86752841Sodium triethylphosphonoacetate

生成物 1

HCID 23225440Ethyl trans-3, 5-di-t-butylcinnamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 0.3 g of the aldehyde prepared above in THF (1 mL) was added to a solution of sodium triethylphosphonoacetate prepared by combining triethylphosphonoacetate (0.37 g, 1.2 eq.) and NaH (0.1 g, 50% dispersion, 1.5 eq.) in THF (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour and then quenched with saturated ammonium chloride and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate and evaporated to give ethyl trans-3, 5-di-t-butylcinnamate as a yellow oil used directly for the next step.

後処理

  1. customprepared
  2. customat 0° C
  3. customquenched with saturated ammonium chloride and ethyl acetate
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-9a3b960ee199418c83434a6b69306a40
出典データセット
uspto-grants-1998_06
特許番号
US05773421

関連ノート

読み込み中…