1,2-Dibromoethane → Methyl 1-(quinolin-6-yl)cyclopropanecarboxylate

HRID 456113ノート

反応式

HRID 456113 の反応式
[Li+].[CH3:2][CH:3]([N-]C(C)C)C.[CH3:9][O:10][C:11](=[O:23])[CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2.BrCCBr>C1COCC1>[CH3:9][O:10][C:11]([C:12]1([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)[CH2:3][CH2:2]1)=[O:23]

参加物

5

反応物 3

HCID 78391,2-DibromoethaneHCID 1514202Methyl 6-quinolineacetateHCID 2724682Lithium diisopropylamide

生成物 1

HCID 58190477Methyl 1-(quinolin-6-yl)cyclopropanecarboxylate収率 20%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of LDA (1.8 M solution in toluene, 14.8 ml, 26.6 mmol) was added dropwise to a solution of quinolin-6-yl-acetic acid methyl ester (2.14 g, 10.64 mmol) in dry THF (40 mL) under a nitrogen atmosphere at −78° C. After 30 min, 1,2-dibromoethane (2.40 g, 12.76 mmol) was added dropwise over 3 min. The resulting mixture was stirred for 1 h at room temperature, then quenched with satd aq. NH4Cl. The mixture was extracted with DCM, washed with brine, dried over Na2SO4, and stripped of solvent. The residue was purified by flash chromatography in silica gel eluting with a EtOAC/hexane gradient to afford 463 mg (20%) of the title compound as yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 8.91 (dd, 1H), 8.12 (d, 1H), 8.07 (d, 1H), 7.77-7.74 (m, 2H), 7.40 (dd, 1H), 3.65 (s, 3H), 1.73-1.71 (m, 2H), 1.33-1.30 (m, 2H). LCMS (method A): [MH]+=228, tR=4.37 min.

後処理

  1. customquenched with satd aq. NH4Cl
  2. extractionThe mixture was extracted with DCM
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe residue was purified by flash chromatography in silica gel eluting with a EtOAC/hexane gradient

出典と根拠

ORDレコード
ord-497dad94ce8749f68ddce116e9d12209
出典データセット
uspto-grants-2013_07
特許番号
US08497368B2

反応ノート

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