Allyl bromide → 3-Allyloxy-5-hydroxybenzoic acid methyl ester

HRID 1177059노트

반응식

HRID 1177059 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C=O)C>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([OH:1])[CH:11]=[C:10]([O:12][CH2:21][CH:20]=[CH2:19])[CH:9]=1

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

생성물 1

HCID 595599953-Allyloxy-5-hydroxybenzoic acid methyl ester수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Methyl 3,5-dihydroxybenzoate (20.9 g, 124 mmol) was dissolved in DMF (30 mL). Potassium carbonate (34.4 g, 249 mmol) was added, followed by allyl bromide (10.5 mL, 124 mmol). The resulting suspension was stirred at room temperature overnight under argon atmosphere. The reaction mixture was quenched with H2O, extracted with EtOAc (2×150 mL). The organic layers were washed with H2O (2×200 mL), dried with MgSO4 and concentrated in vacuo to yield a pale yellow oil which was purified by flash column chromatography eluting with 20% EtOAc in hexane to give a pale yellow solid (10.25 g, 40% yield). 1H NMR (400 MHz, CDCl3) δ 7.08-7.22 (m, 2 H) 6.65 (t, J=2.40 Hz, 1 H) 5.94-6.21 (m, 1 H) 5.73 (s, 1 H) 5.42 (dd, J=17.18, 1.52 Hz, 1 H) 5.31 (dd, J=10.48, 1.39 Hz, 1 H) 4.55 (d, J=5.05 Hz, 2 H) 3.91 (s, 3 H); LCMS for C14H12O4 m/z 209.0 (M+H)+.

후처리

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with EtOAc (2×150 mL)
  3. washThe organic layers were washed with H2O (2×200 mL)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customto yield a pale yellow oil which
  7. customwas purified by flash column chromatography
  8. washeluting with 20% EtOAc in hexane

출처 및 근거

ORD 기록
ord-71638f8d28cc498e84d0504f2fabcc90
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

반응 노트

불러오는 중…