Sodium Iodide → HCID 53864961, compound

HRID 726755Notes

Reaction equation

HRID 726755 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[I-:23].[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.[OH-].[Na+]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]([I:23])=[CH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 521998p-Toluenesulfonic acid monohydrateHCID 19707442HCID 19707442, compound

Product 1

HCID 53864961HCID 53864961, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of acetylene from step 1 (8.79 g, 30 mmol) in dichloromethane (600 mL) at room temperature there was added a solid mixture of sodium iodide (18 g, 120 mmol) and p-toluenesulfonic acid monohydrate (11.4 g, 60 mmol). The mixture was stirred at room temperature for 18 h. The mixture was diluted with aqueous 1N NaOH (600 mL) and stirred vigorously for 15 min. The organic phase was collected and washed 3 times with water, dried and evaporated to a residue which was stirred in a 2:1 mixture of hexane and ether (100 mL) for 2 h and filtered to afford the desired vinyl iodide (8.46 g, 67%) as a beige solid, assayed by NMR to be a 4:1 mixture of Z and E isomers.

Workup

  1. stirringstirred vigorously for 15 min
  2. customThe organic phase was collected
  3. washwashed 3 times with water
  4. customdried
  5. customevaporated to a residue which
  6. stirringwas stirred in a 2:1 mixture of hexane and ether (100 mL) for 2 h
  7. filtrationfiltered

Sources & evidence

ORD record
ord-230b1fcc07da48b69d62adbacdc23599
Source dataset
uspto-grants-1998_01
Patent number
US05710170

Reaction notes

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