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

HRID 850151ノート

反応式

HRID 850151 の反応式
[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

参加物

9

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 15168495Benzeneacetic acid, 2-(bromomethyl)-, methyl esterHCID 1785160256-chloropyridin-2-ol

生成物 1

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

試薬・触媒・溶媒 4

HCID 5238Sodium Iodide触媒HCID 3633615-Crown-5触媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1056a32c409b4d60a2276609862680a4
出典データセット
uspto-grants-2000_01
特許番号
US06015905

反応ノート

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