Tetrahydrofuran → HCID 86591910, compound

HRID 434063Notes

Reaction equation

HRID 434063 reaction equation
[H-].[Na+].C1C[O:6]CC1.[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:10]=1[CH:11]=O.[N+:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])#[C-:19]>CC(O)=O>[CH3:24][O:23][C:21](=[O:22])[C:20]([NH:18][CH:19]=[O:6])=[CH:11][C:10]1[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:9]=1[Cl:8]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 678472-Chloro-6-fluorobenzaldehydeHCID 547815Methyl isocyanoacetate

Product 1

HCID 86591910HCID 86591910, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

NaH (60% in oil, 2.4 g, 0.06 mol, approx. 1.2 eq) was placed in a dry 50 ml flask and heated to 35 degrees. To it was slowly added 50 ml of a THF solution containing 2-chloro-6-fluorobenzaldehyde (7.93 g, 0.05 mol) and methyl isocyanoacetate (5 g, 0.05 mol). The reaction was then cooled to RT, and stirred for 3 hr. At that time, 10 ml of 10% HOAc was added. After 10 min, the contents were concentrated in vacuo to a dark brown oil, then diluted with CHCl3, and transferred to a sep funnel. The aqueous phase was reextracted (3×) with CHCl3, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to crude product. Purification over a pad of silica gel was accomplished by elution with 10:1 CHCl3/EtOAc to afford the title compound, clean Z/E olefins (1:1 mix, 8.24 g, 64%).

Workup

  1. temperatureheated to 35 degrees
  2. waitAfter 10 min
  3. concentrationthe contents were concentrated in vacuo to a dark brown oil
  4. additiondiluted with CHCl3
  5. customtransferred to a sep funnel
  6. washthe combined extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to crude product
  10. customPurification over a pad of silica gel
  11. washwas accomplished by elution with 10:1 CHCl3/EtOAc

Sources & evidence

ORD record
ord-307cad333483411e9e83a8ed107d2823
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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