Cesium carbonate → 1-[2-Hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone

HRID 2267028노트

반응식

HRID 2267028 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[OH:12][C:13]1[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=1[C:23](=[O:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[OH:12][C:13]1[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([O:22][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH:16]=[CH:15][C:14]=1[C:23](=[O:25])[CH3:24]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 27751982',4'-Dihydroxy-3'-propylacetophenone

생성물 1

HCID 684320061-[2-Hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Add 3-bromomethyl nitrobenzene (10.00 g, 46.3 mmol) to a solution of 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (8.99 g, 46.3 mmol) in dimethylformamide (60 mL). After 10 minutes add potassium carbonate (9.60 g, 69.4 mmol) and cesium carbonate (15.08 g, 46.3 mmol). Stir at room temperature for one hour, then heat to 70° C. for 1.5 hours. Cool and add water (250 mL). Triturate for 15 minutes. Filter. Wash the solid with water several times, and then wash with hexanes. Dry to afford the title compound as an off white/light gray powder (12.9 g, 85%): 1H NMR (DMSO-d6) δ 0.91 (t, 3H), 1.52 (m, 2H), 2.58 (s, 3H), 2.63 (m, 2H), 5.42 (s, 2H), 6.72 (d, 1H), 7.73 (t, 1H), 7.83 (d, 1H), 7.90 (d, 1H), 8.21 (d, 1H), 8.34 (s, 1H), 12.88 (bs, 1H).

후처리

  1. temperatureheat to 70° C. for 1.5 hours
  2. temperatureCool
  3. customTriturate for 15 minutes
  4. filtrationFilter
  5. washWash the solid with water several times
  6. washwash with hexanes
  7. customDry

출처 및 근거

ORD 기록
ord-7af9434ab3fb455a94d0b8497cfc6ee5
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858646B2

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