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Sodium Chloride → Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetate

HRID 1492305
ノート
印刷プレビュー

反応式

HRID 1492305 の反応式
Br[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1.[CH2:22]([C:24]1[N:33]=[C:32]([CH2:34][CH3:35])[CH:31]=[C:30]2[C:25]=1[CH2:26][CH2:27][C:28](=O)N2)C.CC(C)([O-:40])C.[K+].O1CCOCCOCCOCCOCCOCC1.[Cl-].[Na+]>O1CCCC1>[CH2:34]([C:32]1[CH:31]=[C:30]([O:40][CH2:2][C:3]2[CH:21]=[CH:20][C:6]([O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=2)[C:25]2[CH2:26][CH2:27][CH2:28][CH2:22][C:24]=2[N:33]=1)[CH3:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 2855718-Crown-6HCID 18952399Ethyl 2-(4-bromomethylphenoxy)phenylacetateHCID 200942545,7-diethyl-3,4-dihydro-1,6-naphthyridin-2(1H)-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 18952389Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetate
収率 18.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of compound C (2.34 g), 5,7-diethyl-1,2,3,4-tetrahydro-1,6-naphthyridin-2-one (1.02 g), potassium t-butoxide (0.57 g) and 1,4,7,10,13,16-hexaoxacyclooctadecane (132 mg) in dry tetrahydrofuran (50 ml) was heated under reflux for 36 hours. Saturated sodium chloride solution (100 ml) was added and the mixture was extracted with ether (2×100 ml). The combined extracts were dried (MgSO4) and concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (3:7 v/v), to give methyl 2-[4-((5,7-diethyl-2-oxo-1,2,3,4-tetrahydro-1,6-naphthyridin-1-yl)methyl)phenoxy]phenylacetate (A) (0.41 g) as an oil; NMR (d6 -DMSO): 1.05-1.25(2×t, 6H), 2.45-2.9(m, 8H), 3.6(s, 3H), 5.0(s, 2H), 5.95(s, 1H), 6.5-7.5(m, 10H).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 36 hours
  3. extractionthe mixture was extracted with ether (2×100 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated by evaporation
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (3:7 v/v)

出典と根拠

ORDレコード
ord-3d1a8b0026aa4c1880f48e5a1a22025c
出典データセット
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05373015

反応ノート

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