Bromocyclopentane → 3-Cyclopentoxy-4-nitrobenzyl alcohol

HRID 327595

반응식

HRID 327595 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].[CH:19]1(Br)[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O>[CH:19]1([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[N+:10]([O-:12])=[O:11])[CH2:5][OH:6])[CH2:23][CH2:22][CH2:21][CH2:20]1

참가 물질

5

반응물 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 145201145-(Hydroxymethyl)-2-nitrophenol

생성물 1

HCID 543467953-Cyclopentoxy-4-nitrobenzyl alcohol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 9.6 g (56.5 mmol) of 3-hydroxy-4-nitrobenzyl alcohol in 960 mL of dry N,N-dimethylformamide under a nitrogen atmosphere was added 11.7 g (83.6 mmol) of anhydrous potassium carbonate followed by 18.1 mL (169.0 mmol) of cyclopentyl bromide. The reaction mixture was warmed to 50° C. for 24 hours after which time the mixture was cooled to room temperature and concentrated to a dark brown residue under high vacuum. The residue was dissolved in 500 mL of chloroform, washed with two, 50 mL portions of saturated sodium chloride, dried over magnesium sulfate, and concentrated to dryness. Purification of the crude product with liquid chromatography over 200 g of silica gel and eluting with 10% methanol in chloroform provided the analytically pure 3-cyclopentoxy-4-nitrobenzyl alcohol upon drying in vacuo.

후처리

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated to a dark brown residue under high vacuum
  3. dissolutionThe residue was dissolved in 500 mL of chloroform
  4. washwashed with two, 50 mL portions of saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customPurification of the crude product with liquid chromatography over 200 g of silica gel
  8. washeluting with 10% methanol in chloroform

출처 및 근거

ORD 기록
ord-8b34d301ec5f4aee878efd87a67d8f23
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274002

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