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Cesium carbonate → 2-(4-Hydroxy-naphthalen-2-yloxy)-2-methyl-propionic acid ethyl ester

HRID 1727013
ノート
印刷プレビュー

反応式

HRID 1727013 の反応式
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH3:27])([O:7][C:8]1[CH:17]=[C:16]([O:18]COCC[Si](C)(C)C)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[CH3:6])[CH3:2].C[Si](C)(C)CCOCOC1C2C(=CC=CC=2)C=C(O)C=1.BrC(C)(C)C(OCC)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.CCO>CCO>[CH2:1]([O:3][C:4](=[O:28])[C:5]([O:7][C:8]1[CH:17]=[C:16]([OH:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)([CH3:27])[CH3:6])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 21887872Ethanol hydrochlorideHCID 690373392-Methyl-2-[4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yloxy]-propionic acid ethyl esterHCID 690383454-(2-Trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ol

生成物 1

HCID 69038379
2-(4-Hydroxy-naphthalen-2-yloxy)-2-methyl-propionic acid ethyl ester
収率 99.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

1.58 g (3.90 mmol) of 2-methyl-2-[4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yloxy]-propionic acid ethyl ester (prepared from 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ol, ethyl bromoisobutyrate, cesium carbonate, in analogy to the procedure described in example 14B] was dissolved in 20 ml of EtOH; then, 1.95 ml of HCl/EtOH-solution (6 molar) was added drop by drop. After 7 hours stirring at room temperature, the solvent was removed by evaporation and the residue was partitioned between water and MeCl2. The organic phase was separated, washed with water, dried (MgSO4) and evaporated. The crude product was purified by chromatography over silica gel with a gradient of AcOEt/heptane to give 1.06 g of pure 2-(4-hydroxy-naphthalen-2-yloxy)-2-methyl-propionic acid ethyl ester as light brown oil.

後処理

  1. customthe solvent was removed by evaporation
  2. customthe residue was partitioned between water and MeCl2
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by chromatography over silica gel with a gradient of AcOEt/heptane

出典と根拠

ORDレコード
ord-03840e410ddc48febfccfc35bb8331ff
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

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート