Borane → 2-(3-Iodophenyl)ethanol

HRID 15892

反応式

HRID 15892 の反応式
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

参加物

5

反応物 3

HCID 6331BoraneHCID 25517Ammonium ChlorideHCID 38702203-Iodophenylacetic acid

生成物 1

HCID 151698502-(3-Iodophenyl)ethanol収率 92.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-43c5c0c66d5a4557aba3851a4a0e8ac7
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

関連ノート

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