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Acetic Acid → 2-(3-Hydroxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

HRID 1727006
ノート
印刷プレビュー

反応式

HRID 1727006 の反応式
[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([O:19]C(OC)=O)[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[O-]CC.[Na+].CC(O)=O>CCO>[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([OH:19])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 690371532-(3-Methoxycarbonyloxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

生成物 1

HCID 690411092-(3-Hydroxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
5 °C

実験手順

1.35 g (4.1 mmol) of 2-(3-methoxycarbonyloxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester was dissolved in 30 ml of EtOH and cooled down to 5° C.; while stirring, 1.66 ml=1.45 g (4.5 mmol) of a solution of sodium ethoxide (21% in EtOH) was added and the reaction mixture then warmed up to ambient temperature. After 1 hour, it was poured into crashed ice/MeCl2, the pH was adjusted to 5-6 with AcOH (1N) and the reaction mixture was subsequently extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, gradient of MeCl2/MeOH) to finally give 0.95 g of the title compound as light brown oil.

後処理

  1. temperaturethe reaction mixture then warmed up to ambient temperature
  2. additionit was poured
  3. extractionthe reaction mixture was subsequently extracted twice with MeCl2
  4. washthe organic phases were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (SiO2, gradient of MeCl2/MeOH) to finally give 0.95 g of the title compound as light brown oil

出典と根拠

ORDレコード
ord-cca1b42930cd47b2836738145e6e8fe1
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07495001B2

反応ノート

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