Hydrochloric Acid → HCID 178516058, 화합물

HRID 585680

반응식

HRID 585680 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 178516058HCID 178516058, 화합물수율 78%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-1de249871154483bb987358323e0405c
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933319B2

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