Tetrahydrofuran → HCID 15652357, compound

HRID 1650081Notes

Reaction equation

HRID 1650081 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH:8]1([Mg]C)[CH2:12][CH2:11][CH2:10][CH2:9]1.[Br-].O1CCC[CH2:17]1>[Cu]I>[CH3:3][C:2]([CH3:5])([C:1](=[O:6])[CH2:17][CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 62493Pivaloyl chlorideHCID 178419575HCID 178419575, compound

Product 1

HCID 15652357HCID 15652357, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

To a stirred mixture of pivaloyl chloride (11.09 g) and copper (I) iodide (10.0 g) in dry tetrahydrofuran (120 mls) at -75° C. under nitrogen was added dropwise cyclopentyl methylmagnesium bromide [prepared from magnesium turnings (3.313 g) and cyclopentylmethylbromide (15.0 g) in dry tetrahydrofuran (95 mls)]. The cooling bath was removed and the reaction mixture stirred for 16 hours then hydrolysed with cold aqueous ammonium chloride (10%). After filtration and extraction of the filtrates with ether, the combined ethereal extracts were washed with aqueous sodium hydroxide (10%) and brine and were dried over anhydrous magnesium sulphate. Concentration in vacuo gave the crude ketone as a yellow oil which was used without further purification. ##STR26##

Workup

  1. customThe cooling bath was removed
  2. filtrationAfter filtration and extraction of the filtrates with ether
  3. washthe combined ethereal extracts were washed with aqueous sodium hydroxide (10%) and brine
  4. dry with materialwere dried over anhydrous magnesium sulphate
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-41f89cfc82af4604b61be857c3981366
Source dataset
uspto-grants-1990_05
Patent number
US04923502

Reaction notes

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