Ethanol → HCID 53766268, compound

HRID 1489780Notes

Reaction equation

HRID 1489780 reaction equation
[Na].C(O)C.[CH:5]1[C:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][C:6]=1[CH:18]=O.[N:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N+:21]=[N-:22]>O1CCCC1>[N:20]([C:23](=[CH:18][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:16][C:17]=2[CH:5]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N+:21]=[N-:22]

Participants

6

Reactant 4

HCID 702EthanolHCID 34804Fluorene-2-carboxaldehydeHCID 69480Acetic acid, azido-, ethyl esterHCID 5360545Sodium

Product 1

HCID 53766268HCID 53766268, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium (1.7 eq) was added to absolute ethanol stirred under nitrogen at room temperature. When dissolution was complete the reaction was cooled to -10° C. and fluorene-2-carboxaldehyde (1 eq) and ethyl azidoacetate (3 eq) dissolved together in the minimum of tetrahydrofuran were added dropwise. The mixture was stirred at -10° C. for 20 h and then quenched by the addition of water and dichloromethane. The combined organic extracts were dried (MgSO4) and evaporated in vacuo. Flash chromatography yielded the pure product (37%) νmax (CHCl3)cm-1 2120 and 1765.

Workup

  1. dissolutionWhen dissolution
  2. temperaturewas cooled to -10° C.
  3. additionwere added dropwise
  4. stirringThe mixture was stirred at -10° C. for 20 h
  5. customquenched by the addition of water and dichloromethane
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cf800f7ed0374f69b27cc4989b5906b9
Source dataset
uspto-grants-1997_10
Patent number
US05679694

Reaction notes

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