Trifluoroacetic acid → 6-bromo-1H,3H-naphtho[1,8-cd]pyran

HRID 2056738

反応式

HRID 2056738 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=O)[O:7][C:8](=O)[C:9]3[C:10]=2[C:11]=1[CH:12]=[CH:13][CH:14]=3.[BH4-].[Na+].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][O:7][CH2:8][C:9]3[C:10]=2[C:11]=1[CH:12]=[CH:13][CH:14]=3

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 664931H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-bromo-HCID 4311764Sodium borohydride

生成物 1

HCID 693072836-bromo-1H,3H-naphtho[1,8-cd]pyran

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To 6-bromo-1H,3H-naphtho[1,8-cd]pyran-1,3-dione (1.5 g, 5.4 mmol) in ethanol (10 mL) was added sodium borohydride (0.41 g, 10.8 mmol) and the mixture stirred at room temperature for 1 h. The reaction was quenched with 3M hydrochloric acid and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in dichloromethane and trifluoroacetic acid (1.05 mL, 13.53 mmol) and triethylsilane (4.3 mL, 27 mmol) added. After stirring for 5 min at room temperature, the solvent was removed in vacuo and the residue purified by column chromatography on silica gel, eluting with dichloromethane, to yield 6-bromo-1H,3H-naphtho[1,8-cd]pyran as a white solid.

後処理

  1. customThe reaction was quenched with 3M hydrochloric acid
  2. extractionextracted into dichloromethane
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. stirringAfter stirring for 5 min at room temperature
  7. customthe solvent was removed in vacuo
  8. customthe residue purified by column chromatography on silica gel
  9. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-93f7594914514440b42af07036f86d83
出典データセット
uspto-grants-2008_02
特許番号
US07335660B2

関連ノート

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