Borane → (4-(Ethylsulfonyl)phenyl)methanol

HRID 2101417

반응식

HRID 2101417 반응식
[CH2:1]([S:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].B>C1COCC1.CO>[CH2:1]([S:3]([C:6]1[CH:14]=[CH:13][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2]

참가 물질

5

반응물 2

HCID 6331BoraneHCID 1793674-Ethylsulfonylbenzoic acid

생성물 1

HCID 572424(4-(Ethylsulfonyl)phenyl)methanol수율 90%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

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온도
70 °C

실험 절차

To a stirring solution of 4-(ethylsulfonyl)benzoic acid (500 mg, 2.33 mmol) in THF (5 mL) at 0° C. under argon was added 1 M borane in THF solution (3.5 mL, 3.5 mmol). The reaction mixture was stirred at 70° C. for 20 min. The reaction mixture was then cooled to room temperature, and the THF was removed under reduced pressure. The residue thus obtained was diluted with methanol (5 mL) and stirred for 5 min. Methanol was then removed under reduced pressure. This process was repeated two more times to ensure complete methanolysis of any borane complex. After residual solvent removal under vacuum, 420 mg of the title compound was obtained as a colorless gum. HPLC/MS: retention time=1.373 min, [M+H]+=201.

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customthe THF was removed under reduced pressure
  3. customThe residue thus obtained
  4. stirringstirred for 5 min
  5. customMethanol was then removed under reduced pressure
  6. customAfter residual solvent removal under vacuum

출처 및 근거

ORD 기록
ord-21b31bf49666462ba77751cc0b5fffaa
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572808B2

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