Sodium Iodide → HCID 22841023, compound

HRID 414783Notes

Reaction equation

HRID 414783 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[I-].[Na+].C([O:14][CH2:15][C@H:16]1[C@@H:21]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][CH2:19][CH2:18][O:17]1)C1C=CC=CC=1.C(#N)C>C(Cl)Cl.O>[CH2:23]([S:22][C@H:21]1[CH2:20][CH2:19][CH2:18][O:17][C@H:16]1[CH2:15][OH:14])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6451240Aluminum(III) ChlorideHCID 22841015HCID 22841015, compound

Product 1

HCID 22841023HCID 22841023, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

6.49 g of aluminum chloride, 7.29 g of sodium iodide and a solution of 2.250 g of dl-cis-2-benzyloxymethyl-3-hexadecylthiotetrahydropyran (prepared as described in Preparation 17) in 50 ml of methylene chloride were added, in that order, to a mixture of 100 ml of acetonitrile and 50 ml of methylene chloride. The reaction mixture was then stirred at room temperature for 2 hours, after which it was diluted with water, and filtered using a Celite (trade mark) filter aid. The filtrate was extracted with methylene chloride. The extract was washed with an aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride and dried. The extract was then concentrated by evaporation under reduced pressure, and the residue was subjected to column chromatography through 50 g of silica gel. The fraction eluted with mixtures of ethyl acetate and hexane ranging from 1:9 to 1:3 by volume was collected to give 1.736 g of the title compound as white crystals, melting at 52°-53° C. (hexane).

Workup

  1. filtrationfiltered
  2. filtrationfilter aid
  3. extractionThe filtrate was extracted with methylene chloride
  4. washThe extract was washed with an aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride
  5. customdried
  6. concentrationThe extract was then concentrated by evaporation under reduced pressure
  7. washThe fraction eluted with mixtures of ethyl acetate and hexane ranging from 1:9 to 1:3 by volume
  8. customwas collected

Sources & evidence

ORD record
ord-56d4bb0387ab47cdb996635cb232848b
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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