Ethyl chloroformate → Ethyl 1,4-dimethoxy-3-methyl-2-naphthoate

HRID 1375139

反応式

HRID 1375139 の反応式
C([Li])CCC.Br[C:7]1[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[O:20][CH3:21].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>O1CCCC1>[CH3:19][O:18][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:20][CH3:21])=[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:16]=1[CH3:17]

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 2922402-Bromo-1,4-dimethoxy-3-methylnaphthaleneHCID 178418339Butyllithium

生成物 1

HCID 11369352Ethyl 1,4-dimethoxy-3-methyl-2-naphthoate収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

n-Butyl lithium (1.6M in hexanes, 4.1 ml, 6.56 mmol) was added dropwise to 2-bromo-1,4-dimethoxy-3-methylnaphthalene (1.537 g, 5.47 mmol) in tetrahydrofuran (30 ml) at −50° C. The reaction was stirred for 30 min at −50° C. before dropwise addition of ethyl chloroformate (1 ml, 10.46 mmol). The reaction was allowed to warm to 0° C. over 18 h quenched by addition of hydrochloric acid (2N) and extracted with ethyl acetate. The extract was dried (Na2SO4) and the solvent evaporated under vacuum. The residue was purified by SPE (silica, 10 g) eluting with 10% ethyl acetate in cyclohexane to give ethyl 1,4-dimethoxy-2-methylnaphthalene-3-carboxylate (1.33 g, 89%).

後処理

  1. customquenched by addition of hydrochloric acid (2N)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (Na2SO4)
  4. customthe solvent evaporated under vacuum
  5. customThe residue was purified by SPE (silica, 10 g)
  6. washeluting with 10% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-58c8d308fd31452db0c1522c0c54ce8d
出典データセット
uspto-grants-2007_01
特許番号
US07166631B2

関連ノート

読み込み中…