Borane → 2-(3-Iodophenyl)ethanol

HRID 15892

반응식

HRID 15892 반응식
B.[I:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](O)=[O:11])[CH:6]=[CH:7][CH:8]=1.[Cl-].[NH4+]>C1COCC1>[I:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 6331BoraneHCID 25517Ammonium ChlorideHCID 38702203-Iodophenylacetic acid

생성물 1

HCID 151698502-(3-Iodophenyl)ethanol수율 92.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of borane (1M, THF, 2.5 eq., 38.2 mL) was added dropwise to a stirred solution of (3-iodophenyl)acetic acid (4.0 g) in THF (100 mL) cooled to 0 C. The resulting mixture was stirred at 0 C for 1 h then warmed to room temperature and stirred for a further 3 h. The mixture was poured into aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic phases were washed with brine, dried (sodium sulfate) and concentrated. The crude was purified by column chromatography (SPE cartridge, SiO2), using cyclohexane-ethyl acetate (70:30) as eluent to afford the title compound (3.5 g, 92% yield).

후처리

  1. temperaturecooled to 0 C
  2. stirringstirred for a further 3 h
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe crude was purified by column chromatography (SPE cartridge, SiO2)

출처 및 근거

ORD 기록
ord-43c5c0c66d5a4557aba3851a4a0e8ac7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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