Methyl 5-nitro-2-furoate → HCID 58526527, compound

HRID 522513Notes

Reaction equation

HRID 522513 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Li+].[Cl-].Br[CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1.C([Cu])#N>C1COCC1>[CH:21]1([C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[O:8][C:7]=2[C:9]([O:11][CH3:12])=[O:10])[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]1

Participants

6

Reactant 4

HCID 94882Methyl 5-nitro-2-furoateHCID 1370573-BromocyclohexeneHCID 433294Lithium ChlorideHCID 178418546HCID 178418546, compound

Product 1

HCID 58526527HCID 58526527, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

Methyl 5-nitrofuran-2-carboxylate (24) (171 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25° C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. After cooling down to −50° C., 3-bromocyclohexene (209 mg, 1.3 mmol) and CuCN.2LiCl (1.0 M solution in THF, 5 drops) were added and the resulting mixture was stirred for 1 h at this temperature. The reaction mixture was quenched with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:2) furnished compound 26 (179 mg, 72%) as a yellowish oil.

Workup

  1. customThe reaction mixture was quenched with a sat. aq. NH4Cl solution (20 mL)
  2. extractionextracted with diethyl ether (3×50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration
  5. customthe solvent was evaporated in vacuo
  6. customPurification by flash-chromatography (CH2Cl2/n-pentane, 1:2)

Sources & evidence

ORD record
ord-7d111bd2bd3d463494a0be5ff10dece8
Source dataset
uspto-grants-2016_05
Patent number
US09334237B2

Reaction notes

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