Imidazole → HCID 67906915, compound

HRID 982477Notes

Reaction equation

HRID 982477 reaction equation
[OH:1][CH:2]([CH3:40])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][CH2:20][CH2:21]Br)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].[NH:41]1[CH:45]=[CH:44][N:43]=[CH:42]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][CH:2]([CH3:40])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:41]2[CH:45]=[CH:44][N:43]=[CH:42]2)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 15078314HCID 15078314, compound

Product 1

HCID 67906915HCID 67906915, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of trans-2-[3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-(4-bromobutoxy)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (64 mg, 0.10 mmol)(Example 19C), imidazole (27 mg, 0.40 mmol) and potassium carbonate (55 mg, 0.40 mmol) in acetone (3 mL) was heated with stirring at 60° C. under nitrogen for 24 h. The reaction mixture was evaporated and the residue was partitioned between dichloromethane and water. The organic layer was washed with water and brine, dried, and evaporated to a residue Purification by preparative TLC (CH2Cl2 -MeOH; 92:8, v/v) gave the title compound: Rf 0.5; MS, m/z 632 M30 . ; NMR (CDCl3) δ 1.28 (bd, CH2CHOHCH3), 6.94 and 7.08 (bs, NCH=CHN).

Workup

  1. temperaturewas heated
  2. customThe reaction mixture was evaporated
  3. customthe residue was partitioned between dichloromethane and water
  4. washThe organic layer was washed with water and brine
  5. customdried
  6. customevaporated to a residue Purification by preparative TLC (CH2Cl2 -MeOH; 92:8, v/v)

Sources & evidence

ORD record
ord-d5c2664ec8144108aefae39712599a1f
Source dataset
uspto-grants-1991_02
Patent number
US04996203

Reaction notes

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