Sodium Iodide → HCID 20273728, compound

HRID 371330Notes

Reaction equation

HRID 371330 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]12[O:12][CH2:11][C:8]([CH3:13])([CH2:9][O:10]1)[CH2:7][O:6]2.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+].[Na+].[I-:39]>C(#N)C>[I-:39].[CH3:13][C:8]12[CH2:11][O:12][C:5]([CH2:4][CH2:3][CH2:2][P+:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)([O:10][CH2:9]1)[O:6][CH2:7]2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 11206544AGN-PC-004CQ8

Product 1

HCID 20273728HCID 20273728, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Intermediate 22 (5 g), triphenylphosphine (33.6 g), NaHCO3 (7 g) and NaI (19.3 g) in acetonitrile (175 ml) was heated under reflux for 17 h. After cooling the inorganic solids were filtered off and washed with dichloromethane. The combined filtrates were evaporated and the residue was triturated firstly with ER (discarded) and then with CH2Cl2. The CH2Cl2 extracts were evaporated in vacuo and the residue, which solidified on trituration with ER, was crystallised from EA-acetonitrile to give the title compound (8.1 g) m.p. 189°-191°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 h
  3. temperatureAfter cooling the inorganic solids
  4. filtrationwere filtered off
  5. washwashed with dichloromethane
  6. customThe combined filtrates were evaporated
  7. customthe residue was triturated firstly with ER (discarded)
  8. customThe CH2Cl2 extracts were evaporated in vacuo
  9. customwas crystallised from EA-acetonitrile

Sources & evidence

ORD record
ord-517b37155fd6425fa1de5169ed3d1712
Source dataset
uspto-grants-1985_07
Patent number
US04530925

Reaction notes

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