Toluene → Tetrahydrofuran toluene

HRID 1264188Notes

Reaction equation

HRID 1264188 reaction equation
[Na][CH:2]([C:6]([O-])=O)[C:3]([O-])=[O:4].[C:9]([O-])(=O)CC([O-])=O.[H-].[Na+].[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.CCOCC.O>[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:6]1[CH2:9][O:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 9084Malonate IonHCID 24758Sodium hydrideHCID 178525821HCID 178525821, compound

Product 1

HCID 22635083Tetrahydrofuran toluene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A solution of Mo(CO)3(EtCN)3 and ligand in toluene was heated at 60-70° C. for 1 h. A solution of sodiomalonate (prepared by adding the malonate to sodium hydride (60% dispersion in oil)) and the substrate in THF was added dropwise via syringe at 60° C. and the mixture was heated at 80-90° C. for the time indicated. The reaction mixture was diluted with ether (5 mL) and water (5 mL) was added. The layers were separated and the aqueous layer was extracted with ether (3×10 mL). The combined organic layers were washed with brine (10 mL), dried over magnesium sulfate and the solvent removed in vacuo. Flash chromatography (with the solvent system indicated) afforded the product as a mixture of the two regioisomers.

Workup

  1. additionwas added dropwise via syringe at 60° C.
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (3×10 mL)
  5. washThe combined organic layers were washed with brine (10 mL)
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed in vacuo
  8. customafforded the product
  9. additionas a mixture of the two regioisomers

Sources & evidence

ORD record
ord-7003fd9dc9ca4ee9961eae3b20578111
Source dataset
uspto-grants-2003_04
Patent number
US06541655B2

Reaction notes

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