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

HRID 964928

Reaction equation

HRID 964928 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9a3b960ee199418c83434a6b69306a40
Source dataset
uspto-grants-1998_06
Patent number
US05773421

Linked notes

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