Hydrochloric Acid → 8-(3,5-Difluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1406830노트

반응식

HRID 1406830 반응식
[Mg].[F:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([F:9])[CH:8]=1.[CH2:11]1[O:21][C:14]2([CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]2)[O:13][CH2:12]1.Cl>C1COCC1.C1(C)C=CC=CC=1.O>[CH2:12]1[O:13][C:14]2([CH2:19][CH2:18][C:17]([C:5]3[CH:4]=[C:3]([F:2])[CH:8]=[C:7]([F:9])[CH:6]=3)([OH:20])[CH2:16][CH2:15]2)[O:21][CH2:11]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

생성물 1

HCID 573701578-(3,5-Difluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol수율 102.9%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매3회

실험 절차

In an argon atmosphere, 20.3 g of magnesium was suspended in THF (40 mL), and a solution of 3,5-difluorobromobenzene (149 g) in THF (450 mL) was added dropwise to the resultant suspension at an inside temperature of 40 to 65° C. After stirring at room temperature for 1 hour, a solution of 1,4-cyclohexanedione monoethylene ketal (100 g) in THF (300 mL) was added dropwise at an inside temperature of 40 to 60° C., followed by stirring at room temperature for 1 hour. Then, water (250 mL), 10% hydrochloric acid (200 mL), and 750 mL of toluene were added in that order, and the mixture was stirred at room temperature for 30 minutes to separate an organic layer. The organic layer was washed with saturated brine two times, and then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to yield 178 g of 4-(3,5-difluorophenyl)-4-hydroxycyclohexanone ethylene ketal as a light yellow solid.

후처리

  1. stirringby stirring at room temperature for 1 hour
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customto separate an organic layer
  4. washThe organic layer was washed with saturated brine two times
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-bfc67301c8c84ee6a37b9f54bc882be3
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916718B2

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