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

HRID 922188ノート

反応式

HRID 922188 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-007197abdec54f5ba21618a455d5b049
出典データセット
uspto-grants-2016_03
特許番号
US09278915B2

反応ノート

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