Tetrahydrofuran → HCID 11299597, compound

HRID 991863Notes

Reaction equation

HRID 991863 reaction equation
I[C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])=[CH:4][CH:3]=1.[NH4+].[Cl-].[CH2:19]1COC[CH2:20]1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:19]([C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])=[CH:4][CH:3]=1)#[CH:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 11290981Benzoic acid, 4-iodo-, 2-(trimethylsilyl)ethyl ester

Product 1

HCID 11299597HCID 11299597, compound

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Procedure

A solution of (trimethylsilyl)ethyl 4-iodobenzoate (2.5 g, 7.2 mmol), (tributyltin)acetylene (2.5 mL, 8.6 mmol) and THF (50 mL) was purged with argon for 10 minutes, and then treated with bis(triphenylphosphine)palladium (II) chloride (126 mg, 0.18 mmol). The suspension was stirred overnight at room temperature and then for 1 hour at 50° C. The solution was treated with NH4Cl and the product extracted with 50% ethyl acetate and hexane solution. The layers were separated and the aqueous layer extracted twice more with the same organic solution. The combined organic layers were washed with brine, and dried (MgSO4), filtered and the solvents were removed under reduced pressure. The residue was purified by silica gel chromatography (98:2, hexane:ethyl acetate) to give the title compound as a yellow oil.

Workup

  1. waitfor 1 hour at 50° C
  2. extractionthe product extracted with 50% ethyl acetate and hexane solution
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted twice more with the same organic solution
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customThe residue was purified by silica gel chromatography (98:2, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-a17572ba21894cbf8ce2c405e63f7b55
Source dataset
uspto-grants-2002_10
Patent number
US06465646B1

Reaction notes

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