Potassium sodium tartarate → [1-(2,6-Dichlorobenzyl)-1H-imidazol-5-yl]methanol

HRID 714628Notes

Reaction equation

HRID 714628 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[CH2:4][N:5]1[C:9]([C:10](OCC)=[O:11])=[CH:8][N:7]=[CH:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.C(OCC)(=O)C>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:2]([Cl:1])[C:3]=1[CH2:4][N:5]1[C:9]([CH2:10][OH:11])=[CH:8][N:7]=[CH:6]1

Participants

6

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 67407845Ethyl 1-(2,6-dichlorobenzyl)-1H-imidazol-5-carboxylate

Product 1

HCID 67409440[1-(2,6-Dichlorobenzyl)-1H-imidazol-5-yl]methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

220 mg (0.74 mmol) of the compound from Example 32A were dissolved in 3 ml of THF, and 0.74 ml (0.74 mmol) of a 1 M solution of lithium aluminum hydride in THF was added dropwise at 0° C. The mixture was stirred at RT for 1 h. For work-up, 5 ml of a saturated potassium sodium tartrate solution were added with ice cooling, the mixture was diluted with 10 ml of ethyl acetate and the precipitated solid was filtered off. The crude product was purified chromatographically [Method 19]. This gave 188 mg (99% of theory) of the target compound.

Workup

  1. filtrationthe precipitated solid was filtered off
  2. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-2e65ef34618443cc8a71a38ec0be8312
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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