Water → Methyl 2-(6-bromopyrid-2-yloxymethyl)phenylacetate

HRID 850157

반응식

HRID 850157 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[OH-].[Na+].Cl[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21].O>C1OCCOCCOCCOCCOC1.C1(C)C=CC=CC=1.CN(C=O)C.[I-].[Na+]>[Br:8][C:4]1[N:3]=[C:2]([O:1][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:7]=[CH:6][CH:5]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 9855748Methyl 2-[2-(chloromethyl)phenyl]acetateHCID 178515930HCID 178515930, 화합물

생성물 1

HCID 19366333Methyl 2-(6-bromopyrid-2-yloxymethyl)phenylacetate수율 51.2%

시약·촉매·용매 4

HCID 5238Sodium Iodide촉매HCID 3633615-Crown-5촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-hydroxy-6-bromopyridine (1.3 g, 7.5 mmol), sodium hydroxide (0.36 g, 9.0 mmol) and 15-crown-5 (1 drop) in dry toluene (20 ml) were stirred at reflux for 1.5 hours. The toluene was removed under reduced pressure and the white salt residue was dissolved in dry DMF (10 ml). Methyl 2-chloromethylphenylacetate (1.0 g, 5 mmol) in dry DMF (10 ml) was added dropwise along with sodium iodide (10 mg). The mixture was stirred at 80° C. for 2 hours, poured into water and extracted with diethyl ether. The ether extracts were washed with water, dried and the ether removed in vacuo leaving an orange oil which was purified by column chromatography (silica eluted with 10% ethyl acetate in hexane) to give methyl 2-(6-bromopyrid-2-yloxymethyl)phenylacetate (0.86 g, 51%) (Compound No. 2 in Table 1) as an orange oil; 1H NMR (270 MHz)δ: 3.68(3H,s), 3.73(2H,s), 5.38(2H,s), 6.68(1H,d), 7.06(1H,d), 7.25-7.50(5H,m) ppm.

후처리

  1. temperatureat reflux for 1.5 hours
  2. customThe toluene was removed under reduced pressure
  3. dissolutionthe white salt residue was dissolved in dry DMF (10 ml)
  4. stirringThe mixture was stirred at 80° C. for 2 hours
  5. extractionextracted with diethyl ether
  6. washThe ether extracts were washed with water
  7. customdried
  8. customthe ether removed in vacuo
  9. customleaving an orange oil which
  10. customwas purified by column chromatography (silica eluted with 10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-2d2c758f19d640058b0f3b90bd5eaee6
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06015905

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