Imidazole → HCID 21781550, compound

HRID 1196639Notes

Reaction equation

HRID 1196639 reaction equation
[I:1]I.O[CH2:4][CH2:5][CH:6]1[CH2:10][C:9]2[C:11]([CH3:18])=[C:12]([OH:17])[C:13]([CH3:16])=[C:14]([CH3:15])[C:8]=2[O:7]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[K+].[Br-]>C1(C)C=CC=CC=1>[I:1][CH2:4][CH2:5][CH:6]1[CH2:10][C:9]2[C:11]([CH3:18])=[C:12]([OH:17])[C:13]([CH3:16])=[C:14]([CH3:15])[C:8]=2[O:7]1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 253877Potassium BromideHCID 14343818HCID 14343818, compound

Product 1

HCID 21781550HCID 21781550, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

4.4 g of iodine are added to a mixture of 3.1 g of 2-(RS)-2-hydroxyethyl-2,3-dihydro-5-hydroxy-4,6,7-trimethylbenzofurane, 5.5 g of triphenylphosphine and 1.4 g of imidazol in 60 ml of toluene. The mixture is stirred for 3 hours at 60° C. The imidazole*HBr is then filtered out and the filtrate is evaporated. After purification by a column chromatography (SiO2), 3.0 g of white solid are obtained. m.p. 96°-97° C.; IR (KBr): 3403 (νOH), 1195 cm-1 (w CH2I); 1H-NMR (CCl4): δ4.9-4.4 (1H,m), 4.0 (1H,s), 3.2 (2H,t), 3.0-2.5 (2H,m), 2.2 (2H,m), 2.1 (9H,s).

Workup

  1. filtrationThe imidazole*HBr is then filtered out
  2. customthe filtrate is evaporated
  3. customAfter purification by a column chromatography (SiO2), 3.0 g of white solid
  4. customare obtained

Sources & evidence

ORD record
ord-d467d1758c64429ab31e91a772816967
Source dataset
uspto-grants-1992_05
Patent number
US05114966

Reaction notes

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