Tetrahydrofuran → HCID 19769935, compound

HRID 2372952Notes

Reaction equation

HRID 2372952 reaction equation
[Li+].CC[CH2:4][CH2-:5].C([CH:8](CC)[P:9]([O-:12])(=[O:11])[O-:10])C.[CH2:15]([N:19]=[C:20]=[S:21])[CH:16]([CH3:18])[CH3:17].O1CC[CH2:24][CH2:23]1>>[CH2:15]([NH:19][C:20](=[S:21])[CH2:8][P:9]([O:10][CH2:4][CH3:5])([O:12][CH2:23][CH3:24])=[O:11])[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 61028n-Butyl lithiumHCID 68960Isobutyl isothiocyanateHCID 18522863HCID 18522863, compound

Product 1

HCID 19769935HCID 19769935, compound

Procedure

N-Butyllithium (62.5 ml, 0.1 mol) was added at 70° C. to diethylmethane-phosphonate (15.2 g, 0.1 mol) in tetrahydrofuran (THF) (200 ml). After 30 minutes, isobutylisothiocyanate (5.8 g, 0.05 mol) in THF (50 ml) was added. The mixture was left overnight at room temperature then poured onto ice water and extracted with ether. The ether solution was washed with brine and dried and the solvents were removed to give an orange oil which was used after further purification. TLC: Silica, ether, 1 spot RF=0.17.

Workup

  1. waitThe mixture was left overnight at room temperature
  2. additionthen poured onto ice water
  3. extractionextracted with ether
  4. washThe ether solution was washed with brine
  5. customdried
  6. customthe solvents were removed
  7. customto give an orange oil which
  8. customafter further purification

Sources & evidence

ORD record
ord-0b2196ead2bf41c98a0f721d78c86c07
Source dataset
uspto-grants-1992_03
Patent number
US05101071

Reaction notes

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