Sodium borohydride → 3-Cyano-6-((4-methoxybenzyl)oxy)-1-(3-hydroxyprop-2-en-1-yl)benzene

HRID 1700287노트

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HRID 1700287 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=[O:22])[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2].[BH4-].[Na+]>C(Cl)Cl.CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH2:19][CH:20]=[CH:21][OH:22])[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 734371553-Cyano-6-((4-methoxybenzyl)oxy)-1-(2-formylethenyl)benzene

생성물 1

HCID 700736253-Cyano-6-((4-methoxybenzyl)oxy)-1-(3-hydroxyprop-2-en-1-yl)benzene수율 3,985.7%

시약·촉매·용매 1

HCID 21958822Dichloromethane methanol water용매

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온도
0 °C

실험 절차

To 3-cyano-6-((4-methoxybenzyl)oxy)-1-(2-formylethenyl)benzene (2.30 g) in 100 mL solution of CH2Cl2/MeOH/H2O (2:7:1) was added NaBH4 (0.29 g) at 0° C. The resulting solution was stirred at 0° C. for 1 hour and concentrated. The resulting residue was diluted with 100 mL of saturated aqueous NaHCO3 and extracted with ethyl acetate (3×). The organic layer was dried, concentrated to afford 3-cyano-6-((4-methoxybenzyl)oxy)-1-(3-hydroxyprop-2-en-1-yl)benzene (92.3 g) as a yellow solid.

후처리

  1. concentrationconcentrated
  2. additionThe resulting residue was diluted with 100 mL of saturated aqueous NaHCO3
  3. extractionextracted with ethyl acetate (3×)
  4. customThe organic layer was dried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-84699d1069f149d1b44a43c6f22a0c66
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350761B1

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