Hydrochloric Acid → HCID 178516058、化合物

HRID 585680

反応式

HRID 585680 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1.C(O)C.[BH4-].[Na+].Cl>C(OCC)(=O)C>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 99424894-(2,4-Dihydroxyphenyl)cyclohexanone

生成物 1

HCID 178516058HCID 178516058、化合物収率 78%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

4-(2,4-Dihydroxyphenyl)cyclohexanone (18 mg) was placed in a round-bottomed flask equipped with magnetic stirrer. Ethanol (5 ml) was added, followed by sodium borohydride (3.3 mg), and the reaction mixture was stirred for 16 hr. Aqueous HCl (20 ml, 1M), followed by ethyl acetate (20 ml), was added, and the organic phase removed and washed with brine (15 ml), dried over anhydrous magnesium sulphate, filtered, and then concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petroleum ether, 60:40, v/v) to afford the title compound (14 mg, 78%) as a white solid. δH (CD3OD) 1.38-1.56 (4H, m), 1.85-1.88 (2H, m), 2.04-2.07 (2H, m), 2.80 (1H, tt), 3.58-3.65 (1H, m), 6.24-6.29 (2H, m), 6.90 (1H, d); m/z (ES−) 267 ((M+AcOH)−1)

後処理

  1. customequipped with magnetic stirrer
  2. additionwas added
  3. customthe organic phase removed
  4. washwashed with brine (15 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petroleum ether, 60:40

出典と根拠

ORDレコード
ord-1de249871154483bb987358323e0405c
出典データセット
uspto-grants-2005_08
特許番号
US06933319B2

関連ノート

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