Hydrochloric Acid → 6-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

HRID 20054

反応式

HRID 20054 の反応式
[C:1](O)(=O)CC(O)=O.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)O[C:14]([C:19]([F:22])([F:21])[F:20])=[CH:13]/[C:12]/2=N/CC1C=CC=CC=1.CCO.[OH2:34].Cl.[OH2:36]>O1CCOCC1>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:34][C:14]([CH3:1])([C:19]([F:20])([F:21])[F:22])[CH2:13][C:12]2=[O:36]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 962WaterHCID 19096565Water ethanolHCID 178506234HCID 178506234、化合物

生成物 1

HCID 673056026-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of malonic acid (1.2 ml, 19 mmol) and (Z)-N-(6-bromo-2-(trifluoromethyl)-4H-chromen-4-ylidene)(phenyl)methanamine (6.63 g, 17 mmol) in dioxane was heated to reflux for 18 h until the reaction was completed. The mixture was cooled to RT and treated with 50% EtOH/H2O (20 ml) followed by conc. HCl (5.0 ml). The resulted mixture was left to stand at RT for 40 min, and then diluted with water (500 ml). The product was extracted with hexane (3×300 ml). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-10% EtOAc/hexane) to afford the title compound as yellow oil. MS m/z: 310 (M+1).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 18 h until the reaction
  3. waitThe resulted mixture was left
  4. extractionThe product was extracted with hexane (3×300 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel column (2-10% EtOAc/hexane)

出典と根拠

ORDレコード
ord-c3a2be2fa62a4184bb7028072a2a91f8
出典データセット
uspto-grants-2010_06
特許番号
US07745484B2

関連ノート

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