Hydrochloric Acid → 1-{2-[4-(Benzyloxy)phenyl]ethyl}cyclobutanol

HRID 384477ノート

反応式

HRID 384477 の反応式
[Mg].II.[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19]Br)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:21]1(=[O:25])[CH2:24][CH2:23][CH2:22]1.Cl>C1COCC1>[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:21]2([OH:25])[CH2:24][CH2:23][CH2:22]2)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 14496CyclobutanoneHCID 5462224MagnesiumHCID 166388271-(Benzyloxy)-4-(2-bromoethyl)benzene

生成物 1

HCID 595275641-{2-[4-(Benzyloxy)phenyl]ethyl}cyclobutanol収率 20.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
50 °C

実験手順

To a mixture of magnesium (35 mg) and THF (1.5 mL) was added one grain of iodine under nitrogen flow, followed by warming in an oil bath at 50° C. A solution of 1-(benzyloxy)-4-(2-bromoethyl)benzene (400 mg) in THF (3 mL) was added dropwise to the mixture over 20 minutes, and then the reaction liquid was heated under reflux for 4 hours. The reaction liquid was ice-cooled, and a solution of cyclobutanone (100 mg) in THF (4 mL) was added dropwise over 15 minutes, followed by stirring at room temperature for another 6 hours. The reaction liquid was adjusted to an acidic pH by adding 1M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9:1-1/1) to obtain 1-{2-[4-(benzyloxy)phenyl]ethyl}cyclobutanol (80 mg).

後処理

  1. customthe reaction liquid
  2. temperaturewas heated
  3. temperatureunder reflux for 4 hours
  4. customThe reaction liquid
  5. temperaturecooled
  6. customThe reaction liquid
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9:1-1/1)

出典と根拠

ORDレコード
ord-4ac691e7efd5497fa288597ef77a88f4
出典データセット
uspto-grants-2013_02
特許番号
US08367702B2

反応ノート

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