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

HRID 850151노트

반응식

HRID 850151 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[OH-].[Na+].Br[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+]>[Cl: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 15168495Benzeneacetic acid, 2-(bromomethyl)-, methyl esterHCID 1785160256-chloropyridin-2-ol

생성물 1

HCID 10989960Methyl 2-(6-chloropyrid-2-yloxymethyl)phenylacetate수율 61.4%

시약·촉매·용매 4

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

실험 절차

A mixture of 2-hydroxy6-chloropyridine (0.84 g, 6.5 mmol), sodium hydroxide (0.275 g, 6.9 mmol) and 15-crown-5 (1 drop) in dry toluene (15 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-bromomethylphenylacetate (1.5 g, 6.2 mmol) in dry DMF (10 ml) was added dropwise along with sodium iodide (10 mg). The mixture was stirred at room temperature 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 a yellow oil which was purified by column chromatography (silica eluted with 10 % ethyl acetate in hexane) to give methyl 2-(6-chloropyrid-2-yloxymethyl)phenylacetate (1.11 g, 61%) (Compound No. 1 in Table 1) as a pale yellow oil; 1H NMR(270 MHz)δ:3.67(3H,s), 3.82(2H,s), 5.39(2H,s) 6.65(1H,d), 6.90(1H,d), 7.25-7.55(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 room temperature 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 a yellow oil which
  10. customwas purified by column chromatography (silica eluted with 10 % ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-1056a32c409b4d60a2276609862680a4
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06015905

반응 노트

불러오는 중…