1-Methyl-1H-imidazole-4-carbaldehyde → alpha-(6-Chloro-2,2-dimethyl-4H-1,3-benzodioxin-8-yl)-1-methyl-1H-imidazole-4-methanol

HRID 1194372Notes

Reaction equation

HRID 1194372 reaction equation
Br[C:2]1[C:7]2[O:8][C:9]([CH3:13])([CH3:12])[O:10][CH2:11][C:6]=2[CH:5]=[C:4]([Cl:14])[CH:3]=1.[CH3:15][N:16]1[CH:20]=[C:19]([CH:21]=[O:22])[N:18]=[CH:17]1>>[Cl:14][C:4]1[CH:3]=[C:2]([CH:21]([C:19]2[N:18]=[CH:17][N:16]([CH3:15])[CH:20]=2)[OH:22])[C:7]2[O:8][C:9]([CH3:13])([CH3:12])[O:10][CH2:11][C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 5734191-Methyl-1H-imidazole-4-carbaldehydeHCID 145203368-bromo-6-chloro-2,2-dimethyl-4H-1,3-benzodioxin

Product 1

HCID 14520341alpha-(6-Chloro-2,2-dimethyl-4H-1,3-benzodioxin-8-yl)-1-methyl-1H-imidazole-4-methanolYield 63.5%

Procedure

Starting from 8-bromo-6-chloro-2,2-dimethyl-4H-1,3-benzodioxin and 1-methyl-1H-imidazole-4-carboxaldehyde. The addition of the organomagnesium compound is carried out at 0° C. Yield: 63.5% of theory; M.P.: 131°-136° C. (recrystallized from ethyl acetate).

Workup

  1. customis carried out at 0° C
  2. customM.P.: 131°-136° C. (recrystallized from ethyl acetate)

Sources & evidence

ORD record
ord-fe52e72e1d614ae2ae5a13bfa028848d
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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