Iodine → HCID 19358493, compound

HRID 377323Notes

Reaction equation

HRID 377323 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1.[Mg].II.[CH2:28]([O:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=[O:40])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl-].[NH4+]>O1CCCC1>[C:13]1([C:11]2[N:12]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH:39]([OH:40])[C:38]3[CH:41]=[CH:42][CH:43]=[C:36]([O:35][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:37]=3)[O:9][C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 743423-BenzyloxybenzaldehydeHCID 5462224MagnesiumHCID 14971853HCID 14971853, compound

Product 1

HCID 19358493HCID 19358493, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2-(2-bromophenyl)-4,5-diphenyloxazole (3.0 g) in tetrahydrofuran (15 ml) was added dropwise to a stirred mixture of magnesium (213 mg) and a slight amount of iodine in tetrahydrofuran (15 ml) at room temperature under a nitrogen atmosphere and the resulting mixture was stirred at 70° C. for 3 hours. The reaction mixture was added slowly to a solution of 3-benzyloxybenzaldehyde (1.69 g) in tetrahydrofuran (6 ml) under dry ice-acetone cooling and a nitrogen atmosphere. The resulting mixture was stirred at the same temperature for 3 hours and at room temperature overnight, treated with ammonium chloride aqueous solution, and partitioned between ethyl acetate and 0.5N hydrochloric acid. The organic layer was washed with sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (n-hexane - ethyl acetate) over silica gel to afford 2-(4,5-diphenyl-2-oxazolyl)-3'-benzyloxybenzhydrol (2.21 g) as paste.

Workup

  1. custompartitioned between ethyl acetate and 0.5N hydrochloric acid
  2. washThe organic layer was washed with sodium bicarbonate aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (n-hexane - ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-12515b76295a42f6bb673f764f5b0e16
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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