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

HRID 1015696노트

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HRID 1015696 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 119895722-(Oxolan-2-yl)ethan-1-ol용매

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온도
60 °C

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-90ddb0e3b8184d4b967e30e80fe09290
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985862B2

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