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

HRID 15718

반응식

HRID 15718 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-68ac42a1003a457896b8b3eb493ce566
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732622B2

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