Lithium borohydride → (5-Chloro-2-(methylsulfonyl)phenyl)methanol

HRID 1013950ノート

反応式

HRID 1013950 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[BH4-].[Li+]>O1CCCC1CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([CH2:7][OH:8])[CH:11]=1

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 66877882Methyl 5-chloro-2-(methylsulfonyl)benzoate

生成物 1

HCID 66885987(5-Chloro-2-(methylsulfonyl)phenyl)methanol収率 89.3%

試薬・触媒・溶媒 1

HCID 119895722-(Oxolan-2-yl)ethan-1-ol溶媒

反応条件

温度
60 °C

実験手順

(Step 2) To a solution of methyl 5-chloro-2-(methylsulfonyl)benzoate obtained in Step 1 (2.65 g) in tetrahydrofuran-ethanol (50 ml+5 ml) was added lithium borohydride (348 mg) at 0° C. The mixture was stirred at 60° C. for 2 hr, treated with ice, and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1) to give [5-chloro-2-(methylsulfonyl)phenyl]methanol (2.1 g).

後処理

  1. additiontreated with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

出典と根拠

ORDレコード
ord-25b325d19ca849cca994a74d7d315fb4
出典データセット
uspto-grants-2011_07
特許番号
US07982044B2

反応ノート

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