Diethyl chlorophosphate → HCID 86746475, compound

HRID 1646187Notes

Reaction equation

HRID 1646187 reaction equation
[CH2:1]([O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1)[CH2:2][C:3]#[CH:4].C([Li])CCC.[P:17](Cl)([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18].C(=O)(O)[O-].[Na+]>O1CCCC1>[O:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[O:5][CH2:1][CH2:2][C:3]#[C:4][P:17](=[O:18])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 13139Diethyl chlorophosphateHCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyranHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 86746475HCID 86746475, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of tetrahydro-2-(3-butynyloxy)2H-pyran (20 g, 0.13 mol) in anhydrous tetrahydrofuran (200 ml) is cooled in a dry ice-acetone bath and treated dropwise with n-butyllithium (2.5M in hexane, 0.13 mol) in tetrahydrofuran (20 ml). The anion is stirred for 30 minutes and treated with diethyl chlorophosphate in tetrahydrofuran added via a slow stream. The reaction mixture is stirred 15 minutes and then warmed to room temperature overnight. A saturated aqueous solution of sodium bicarbonate (125 ml) is added and the mixture extracted with ethyl acetate (2×150 ml). The organic layer is separated, dried (magnesium sulfate), filtered and evaporated. The residue is chromatographed over silica gel and eluted with ethyl acetate in chloroform to give the title compound.

Workup

  1. additionadded via a slow stream
  2. stirringThe reaction mixture is stirred 15 minutes
  3. extractionthe mixture extracted with ethyl acetate (2×150 ml)
  4. customThe organic layer is separated
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is chromatographed over silica gel
  9. washeluted with ethyl acetate in chloroform

Sources & evidence

ORD record
ord-df1711ced92f4d5295e95dc98126ee8a
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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