Ethyl diethoxyacetate → methyl 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylate

HRID 1474276ノート

反応式

HRID 1474276 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[CH2:11]([O:13][CH:14]([O:20]CC)[C:15](OCC)=O)C>C[N+]([O-])=O.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][O:10][CH:15]2[C:14]([O:13][CH3:11])=[O:20]

参加物

5

反応物 2

HCID 80169Ethyl diethoxyacetateHCID 27340892-(2-Bromophenyl)ethan-1-ol

生成物 1

HCID 66646338methyl 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylate

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6375Nitromethane溶媒

実験手順

TiCl4 (76 g, 0.4 mol) was added over a period of 10 min to an ice-cooled mixture of 2-(2-bromophenyl)ethanol (20 g, 0.1 mol) and ethyl bis(ethyloxy)acetate (21.1 g, 0.120 mol) in 120 mL of CH3NO2. After stirring for 10 min, the ice bath was removed and the mixture was allowed to stir at room temperature overnight. The mixture was poured into ice/aqueous 1N HCl. Extracted with DCM and backwashed with 1N HCl and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified with silica gel column chromatography to give the product methyl 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylate.

後処理

  1. temperaturecooled
  2. customthe ice bath was removed
  3. stirringto stir at room temperature overnight
  4. additionThe mixture was poured into ice/aqueous 1N HCl
  5. extractionExtracted with DCM
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography

出典と根拠

ORDレコード
ord-71d284e30b2d44d891637f685b3187c8
出典データセット
uspto-grants-2015_04
特許番号
US09018211B2

反応ノート

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