CID 406 → HCID 178445043, compound

HRID 412482Notes

Reaction equation

HRID 412482 reaction equation
[H-].[Na+].[PH:3](=[O:6])([O-:5])[O-:4].[CH2:7]([Li])[CH2:8][CH2:9]C.Br[CH2:13][C:14]#CC.[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>CCCCCC>[CH3:9][CH:8]([CH3:7])[C:19](=[O:20])[CH2:18][CH2:17][C:21]#[C:13][CH3:14].[PH:3](=[O:4])([O-:6])[O-:5]

Participants

7

Reactant 5

HCID 406CID 406HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 178418339Butyllithium

Product 1

HCID 178445043HCID 178445043, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred suspension of dry sodium hydride (3.13 g, 124.07 mmol) in dry THF (100 ml) at room temperature was added dropwise a solution of dimethyl 2-oxopropyl)-phosphonate (20.61 g, 124.07 mmol) in dry THF (50 ml) under N2. The reaction mixture was stirred for 1 h, then cooled in an ice-bath and treated with a solution of n-butyllithium (7.95 g, 124.07 mmol) in hexane, causing a dark brown solution to be formed. Stirring was continued for 1 h at 0° C., followed by dropwise addition of 1-bromo2-butyne.1 (15 g, 112.79 mmol) in THF (30 ml). The reaction mixture was gradually warmed to room temperature and after 1 h (TLC monitoring) the reaction mixture was quenched with ice-water, HCl 1M to pH about 4 and extracted, twice, with ethyl acetate. The organic layer was washed with brine and chromatographed on silica gel using EtOAc as eluent. Rf=0.38 (silica gel, ethylacetate), yield 18 g (73%).

Workup

  1. temperaturecooled in an ice-bath
  2. customto be formed
  3. stirringStirring
  4. waitwas continued for 1 h at 0° C.
  5. customwas quenched with ice-water, HCl 1M to pH about 4
  6. extractionextracted
  7. washThe organic layer was washed with brine
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-38314c868cf642b785ee752fca019b67
Source dataset
uspto-grants-2003_05
Patent number
US06562868B1

Reaction notes

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