Lithium Chloride → [1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol

HRID 714629ノート

反応式

HRID 714629 の反応式
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]=[C:6]1[C:13](OCC)=[O:14].[Cl-].[Li+].[BH4-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>COCCOC>[Cl:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:2]([Cl:1])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]=[C:6]1[CH2:13][OH:14]

参加物

6

反応物 4

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 9855836Potassium sodium tartarateHCID 67409298Ethyl 1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole-2-carboxylate

生成物 1

HCID 67410386[1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

1200 mg (3.5 mmol) of the compound from Example 33A together with 15 mg (0.35 mmol) of lithium chloride were dissolved in 53 ml 1,2-dimethoxyethane, and 198 mg (5.23 mmol) of sodium borohydride were added at 0° C. The mixture was stirred at RT for 1 h. For work-up, 25 ml of a saturated potassium sodium tartrate solution were added with ice cooling and the mixture was extracted with 50 ml of ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1). This gave 800 mg (76% of theory) of the target compound.

後処理

  1. extractionthe mixture was extracted with 50 ml of ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1)

出典と根拠

ORDレコード
ord-dd5f10d1e3d04799aab6c5d482bccdb3
出典データセット
uspto-grants-2015_11
特許番号
US09187466B2

反応ノート

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