Potassium Carbonate → Methyl 2-cyano-3-{4-[(3-hydroxybenzyl)oxy]phenyl}propanoate

HRID 922188노트

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HRID 922188 반응식
[CH3:1][O:2][C:3](=[O:15])[CH:4]([C:13]#[N:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1>C(#N)C>[C:13]([CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:15])#[N:14]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 137401503-(Bromomethyl)phenolHCID 22988437Methyl 2-cyano-3-(4-hydroxyphenyl)propanoate

생성물 1

HCID 66685231Methyl 2-cyano-3-{4-[(3-hydroxybenzyl)oxy]phenyl}propanoate수율 65.44%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a 50 mL RB flask fitted with magnetic stirrer was charged 10 mL of acetonitrile. To the stirred solvent was added 2-cyano-3-(4-hydroxy-phenyl)-propanoic acid methyl ester (0.3 g, 1.57 mmol), followed by K2CO3 (0.65 g, 4.71 mmol) and 3-bromomethyl-phenol (0.294 g, 1.57 mmol). After addition, the RM was heated at 50° C. for 1 h. After 1 h, the RM was concentrated to distill off the solvent, water (20 mL) was added and the aqueous layer was extracted with ethyl acetate (15 mL×2). The organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The product was obtained as yellow liquid. (0.32 g, yield: 65.44%); MS (ESI, 120 eV): m/z=310.0 (M−H)+.

후처리

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. additionAfter addition
  3. concentrationthe RM was concentrated
  4. distillationto distill off the solvent, water (20 mL)
  5. additionwas added
  6. extractionthe aqueous layer was extracted with ethyl acetate (15 mL×2)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. customThe solvent was removed under reduced pressure
  9. customThe product was obtained as yellow liquid

출처 및 근거

ORD 기록
ord-007197abdec54f5ba21618a455d5b049
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278915B2

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