Sodium Iodide → HCID 67906665, compound

HRID 1196706Notes

Reaction equation

HRID 1196706 reaction equation
[OH:1][CH:2]([CH3:38])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:21]2[CH2:25][CH2:24][C@H:23]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[O:22]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19]Br)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].[I-].[I-].[Na+].[S:42]1[CH:46]=[CH:45][N:44]=[CH:43]1>CN(C=O)C.C1(C)C=CC=CC=1>[OH:1][CH:2]([CH3:38])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:21]2[CH2:25][CH2:24][C@H:23]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[O:22]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][C:43]2[S:42][CH:46]=[CH:45][N:44]=2)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 9256ThiazoleHCID 30165Iodide IonHCID 15078312HCID 15078312, compound

Product 1

HCID 67906665HCID 67906665, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

trans-2-[3-(2-Hydroxy-n-propylsulfonyl)-4-n-propoxy-5-(2-bromoethoxy) phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (50 mg, 0.08 mmol)(Example 12) was converted into the corresponding iodide by treatment with sodium iodide in DMF. The iodo intermediate and thiazole (0.17 mL, 2.4 mmol) in toluene (5 mL) was heated under reflux overnight. The solution was evaporated to dryness, and the product was isolated by preparative TLC (chloroform-methanol; 9:1, v/v), Rf 0.08.

Workup

  1. temperatureunder reflux overnight
  2. customThe solution was evaporated to dryness
  3. customthe product was isolated by preparative TLC (chloroform-methanol

Sources & evidence

ORD record
ord-c233f18f5e62499f82b53e623a747c4c
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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