Diethyl Ether → HCID 9884273, compound

HRID 1596509Notes

Reaction equation

HRID 1596509 reaction equation
C([Li])CCC.[CH2:6]([N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:18]1(=O)[C:30]2[C:22]([C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:21][CH:20]=[CH:19]1.C([O:34]CC)C>C1COCC1>[CH2:6]([N:13]1[CH:17]=[CH:16][N:15]=[C:14]1[C:29]1([OH:34])[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:30]1=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 779181-BenzylimidazoleHCID 22281833FluoreneoneHCID 178418339Butyllithium

Product 1

HCID 9884273HCID 9884273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

1.2 eq of n-butyllithium are added at −70° C. to N-benzylimidazole in THF. The mixture is allowed to warm to −20° C. in the course of one hour and is then again cooled to −70° C. After addition of 1 eq of fluorenone in THF, it is allowed to warm to RT in the course of 5 h. Aqueous work-up, extraction with EA, followed by subsequent drying of the organic phase over magnesium sulfate and evaporation of the solvents yields a solid, yellowish residue. Trituration with diethyl ether yields a solid, which is filtered off with suction.

Workup

  1. temperatureis then again cooled to −70° C
  2. temperatureto warm to RT in the course of 5 h
  3. extractionAqueous work-up, extraction with EA
  4. dry with materialby subsequent drying of the organic phase over magnesium sulfate and evaporation of the solvents
  5. customyields a solid, yellowish residue
  6. filtrationis filtered off with suction

Sources & evidence

ORD record
ord-6ac8517207fa4f9d92632ee51f4021c4
Source dataset
uspto-grants-2001_09
Patent number
US06291502B1

Reaction notes

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