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

HRID 1845301노트

반응식

HRID 1845301 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ba76b2e10c644971818b87d6f703e7f2
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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