1-(4-Bromophenyl)cyclobutane-1-carboxylic acid → (1-(4-Bromophenyl)cyclobutyl)methanol

HRID 1054739

反応式

HRID 1054739 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](O)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

参加物

4

反応物 1

HCID 167699191-(4-Bromophenyl)cyclobutane-1-carboxylic acid

生成物 1

HCID 58538689(1-(4-Bromophenyl)cyclobutyl)methanol収率 62%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 1-(4-bromophenyl)cyclobutanecarboxylic acid (300 mg, 1.20 mmol) in 1,4-dioxane (5 mL) was added borane dimethylsulfide complex (0.24 mL, 2.4 mmol) dropwise at 0° C. The ice bath was removed, and the reaction mixture was stirred at room temperature for 10 min. The reaction mixture was quenched with methanol (20 mL). The organic solvents were removed under reduced pressure to give a residue, which was dissolved in ethyl acetate, then washed with brine. The organic phase was concentrated to give [1-(4-bromophenyl)cyclobutyl]methanol (170 mg, 62% yield) as a yellow oil which was used directly in the next step.

後処理

  1. customThe ice bath was removed
  2. customThe reaction mixture was quenched with methanol (20 mL)
  3. customThe organic solvents were removed under reduced pressure
  4. customto give a residue, which
  5. washwashed with brine
  6. concentrationThe organic phase was concentrated

出典と根拠

ORDレコード
ord-a43ab158e3014363b8dc7631e25448f1
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

関連ノート

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