Methanol → HCID 15869808, compound

HRID 369119Notes

Reaction equation

HRID 369119 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[CH3:24])=[O:8].O1CCCC1.CO.[BH4-].[Na+]>[Cl-].[Na+].O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)[OH:8])=[C:18]([CH3:24])[CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 18332482HCID 18332482, compound

Product 1

HCID 15869808HCID 15869808, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 1.02 g (3 mmol) of 2-(4-chloro-2-methylphenoxymethyl)phenyl 1-methylimidazol-2-yl ketone, 6 ml of tetrahydrofuran and 3 ml of methanol was added 0.11 g (3 mmol) of sodium borohydride under ice-cooling and stirred at room temperature for an hour. After completion of the reaction, 100 ml of brine was added and extracted twice with 50 ml of dichloromethane. The extract was dried over anhydrous magnesium and concentrated under reduced pressure. The crystal thus obtained was recrystallized from ethyl acetate to give 2-[2-(4-chloro-2-methylphenoxymethyl)-α-hydroxybenzyl]-1-methylimidazole (0.57 g, 55.4%) as colorless crystals. mp. 159-160° C.

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionextracted twice with 50 ml of dichloromethane
  4. dry with materialThe extract was dried over anhydrous magnesium
  5. concentrationconcentrated under reduced pressure
  6. customThe crystal thus obtained
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-62a9b4bd298f40ac9a95eb7ac1d58b89
Source dataset
uspto-grants-2000_10
Patent number
US06136837

Reaction notes

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