Hydrochloric Acid → HCID 22415600, compound

HRID 1721459Notes

Reaction equation

HRID 1721459 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([P:14](=[O:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[I:36]I.Cl>C1COCC1.C1COCC1.CCCCCCC.C(OCC)(=O)C>[I:36][C:4]1[C:5]2[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=[CH:2][C:3]=1[P:14](=[O:27])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 2724682Lithium diisopropylamideHCID 22415596HCID 22415596, compound

Product 1

HCID 22415600HCID 22415600, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 21263495Tetrahydrofuran heptaneSolvent

Conditions

Temperature
-78 °C

Procedure

9.8 g of (dibenzofuran-3-yl)-diphenyl-phosphine oxide in 100 ml of THF are admixed with 13.3 ml of a 2M solution of lithium diisopropylamide in THF/n-heptane and stirred for a further 10 minutes at -78° C. A solution of 7.9 g of iodine in 30 ml of THF is added at -76° C. Subsequently the mixture is hydrolyzed with 2N HCl, ethyl acetate is added, the solution is washed with sodium thiosulphate solution, water and saturated NaCl solution, dried with MgSO4 and concentrated. 12.7 g (98% of theoretical) of crude product remain.

Workup

  1. additionis added
  2. washthe solution is washed with sodium thiosulphate solution, water and saturated NaCl solution
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5aaee0239c204239873c788f1721f6c0
Source dataset
uspto-grants-1996_04
Patent number
US05510503

Reaction notes

Loading…