tert-Butyl methyl ether → 2-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-

HRID 2544

反応式

HRID 2544 の反応式
[O:1]([CH:9]1[CH2:13][C:12](=[O:14])[CH:11]=[CH:10]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[Mg+2].[Br-].[Br-].[H-].[Al+3].[Li+].[H-].[H-].[H-].COC(C)(C)C>C1(C)C=CC=CC=1>[Si:2]([O:1][C@@H:9]1[CH2:13][C@H:12]([OH:14])[CH:11]=[CH:10]1)([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

参加物

6

反応物 4

HCID 15413tert-Butyl methyl etherHCID 82241Magnesium BromideHCID 41316994-((tert-Butyl(dimethyl)silyl)oxy)cyclopent-2-en-1-oneHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 101767472-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-収率 64.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-25 °C

実験手順

A stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (2.0 g, 9.42 mmol) in anhydrous toluene (15 mL) under an atmosphere of argon is treated with MgBr2 (3.5 g, 19.0 mol). The mixture is cooled to -25° C. and treated with lithium aluminum hydride (178 mg, 4.69 mmol) in one portion, followed by addition of anhydrous tert-butyl methyl ether (3.0 mL). The reaction is stirred at -20° C. for 2 hours and then overnight at room temperature. Additional lithium aluminum hydride (178 mg, 4.69 mmol) is added at room temperature and the reaction is stirred for 2 hours. The reaction is then quenched by slow addition of 1N NaOH (5 mL) followed by filtration through diatomaceous earth. The filtrate is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (1.3 g); cis/trans/1-2 +1-4 addition, 90/3/7.

後処理

  1. customovernight
  2. customat room temperature
  3. stirringthe reaction is stirred for 2 hours
  4. customThe reaction is then quenched by slow addition of 1N NaOH (5 mL)
  5. filtrationfollowed by filtration through diatomaceous earth
  6. dry with materialThe filtrate is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-4213d05daadd4cc1a427b80287607a1d
出典データセット
uspto-grants-1998_03
特許番号
US05728899

関連ノート

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