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

HRID 964928

반응식

HRID 964928 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a3b960ee199418c83434a6b69306a40
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773421

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