Water → Methyl 2'-cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

HRID 1845301ノート

反応式

HRID 1845301 の反応式
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([C:20](OC)=[O:21])[CH:11]=1)#[N:2].[BH4-].[Na+].O>CO>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]([CH2:20][OH:21])[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:15]=1)#[N:2]

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58188054Dimethyl 2'-cyano-4'-methylbiphenyl-3,5-dicarboxylate

生成物 1

HCID 58187956Methyl 2'-cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of dimethyl 2′-cyano-4′-methylbiphenyl-3,5-dicarboxylate (343 mg, 1.05 mmol) in methanol (20 mL) was cooled at 0° C. and sodium tetrahydroborate (0.60 g, 16 mmol) was added slowly. The mixture was stirred at rt for 6 h, and then treated with water (20 mL). The volatiles were removed in vacuo and the acqueous phase was extracted with CH2Cl2 (30 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound.

後処理

  1. customThe volatiles were removed in vacuo
  2. extractionthe acqueous phase was extracted with CH2Cl2 (30 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-ba76b2e10c644971818b87d6f703e7f2
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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