Hydrochloric Acid → HCID 18787929、化合物

HRID 1106373ノート

反応式

HRID 1106373 の反応式
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.[CH2:10]1[O:20][C:13]2([CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=O)[O:12][CH2:11]1.[Cl-].[NH4+].Cl.C1C[O:27]CC1>>[F:9][C:5]1[CH:4]=[C:3]([C:16]2([OH:27])[CH2:17][CH2:18][C:13]3([O:20][CH2:10][CH2:11][O:12]3)[CH2:14][CH2:15]2)[CH:8]=[CH:7][CH:6]=1

参加物

7

反応物 6

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran3 回HCID 140821-Bromo-3-fluorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 123480741,4-Dioxaspiro[4.5]decan-6-one

生成物 1

HCID 18787929HCID 18787929、化合物

反応条件

温度
10 °C

実験手順

48.6 g of magnesium turnings were wetted with 50 ml of THF, and a solution of 350 g of 1-bromo-3-fluorobenzene in 700 ml of THF was then added dropwise with stirring at such a rate that the reaction boiled gently. The mixture was then refluxed for a further 30 minutes and cooled to 10° C., and a solution of 312.4 g of cyclohexanedione monoethylene ketal and 600 ml of THF was added dropwise with stirring. During this addition, the reaction temperature rose to 60° C. The mixture was refluxed for a further 30 minutes and then cooled to room temperature. 800 ml of ammonium chloride solution were then added, and the mixture was neutralized using hydrochloric acid. The organic phase was separated off, and the aqueous phase was extracted once with 300 ml of methyl tert-butyl ether. The combined organic extracts were then washed once with 200 ml of sodium chloride solution, dried using sodium sulfate, filtered and evaporated to a residue, giving 8-(3-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol.

後処理

  1. temperatureThe mixture was then refluxed for a further 30 minutes
  2. stirringwith stirring
  3. additionDuring this addition
  4. customrose to 60° C
  5. temperatureThe mixture was refluxed for a further 30 minutes
  6. temperaturecooled to room temperature
  7. customThe organic phase was separated off
  8. extractionthe aqueous phase was extracted once with 300 ml of methyl tert-butyl ether
  9. washThe combined organic extracts were then washed once with 200 ml of sodium chloride solution
  10. customdried
  11. filtrationfiltered
  12. customevaporated to a residue

出典と根拠

ORDレコード
ord-9ef00141c5ca4eea8fc4288df7ed0200
出典データセット
uspto-grants-2000_05
特許番号
US06057006

反応ノート

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