Ethyl bromoacetate → Ethyl 3-ethoxyphenoxyacetate

HRID 537285

反応式

HRID 537285 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:2]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 693063-Ethoxyphenol

生成物 1

HCID 21506368Ethyl 3-ethoxyphenoxyacetate収率 101.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A 500 mL flask fitted with a stir-bar and septum with an Ar inlet was charged with 3-ethoxyphenol (20.4 g, 148 mmol), K2CO3 (28.5 g, 222 mmol), and DMF (250 mL). To the resultant solution was added ethyl bromoacetate (27.1 g, 18.0 mL, 162 mmol) and the mixture stirred overnight. The solids were filtered off and rinsed with EtOAc (500 mL). The filtrate was washed with saturated aqueous NH4Cl (2×250 mL), H2O (2×250 mL), and brine (200 mL), filtered through phase separation paper, and concentrated in vacuo to give 33.6 g of ethyl 3-ethoxyphenoxyacetate as a colorless oil (100%). 1H NMR (60 MHz, CDCl3): δ 7.2-6.9 (m, 1H), 6.6-6.3 (m, 3H), 4.6 (s, 2H), 4.2 (qt, 2H), 4.0 (qt, 2H), 1.4 (t, 3H), 1.3 (t, 3H) ppm. HPLC analysis (0:10:90 H2O:A1:MeOH) showed a purity of 98% with a retention time of 5.3 min.

後処理

  1. customA 500 mL flask fitted with a stir-bar
  2. filtrationThe solids were filtered off
  3. washrinsed with EtOAc (500 mL)
  4. washThe filtrate was washed with saturated aqueous NH4Cl (2×250 mL), H2O (2×250 mL), and brine (200 mL)
  5. filtrationfiltered through phase separation paper
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-235c00d6b6554ac1a1ce2a0442e24696
出典データセット
uspto-grants-2014_10
特許番号
US08859780B2

関連ノート

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