Butyl Acrylate → Ethyl acetate hexane methanol

HRID 556276ノート

反応式

HRID 556276 の反応式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([O:13][C:14](=[O:17])[CH:15]=C)[CH2:10][CH2:11][CH3:12].[CH3:18][C:19](N(C)C)=[O:20]>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:18][CH2:19][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:9]([O:13][C:14](=[O:17])[CH3:15])[CH3:10].[CH3:19][OH:20]

参加物

6

反応物 3

HCID 8846Butyl AcrylateHCID 31374Dimethylacetamide2 回HCID 62657Potassium Phosphate, Tribasic

生成物 1

HCID 21879739Ethyl acetate hexane methanol収率 47%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

実験手順

A 10 mL Schenk tube was dried in oven and loaded under N2 with K3PO4 (2.37 g, 11.16 mmol) and DMA (2.0 mL). 3-iodobenzaldeide (1.85 g, 7.97 mmol) and n-butylacrylate (2.28 mL, 15.94 mmol) were then added by syringe. A solution of Pd(OAc)2 (0.18 g, 0.797 mmol) in DMA (0.5 mL) was further added by syringe. The Schlenk tube was then sealed under nitrogen and placed in a pre-heated oil bath at 140° C., and the reaction mixture was stirred for 24 h. After cooling to room temperature, the reaction mixture was poured in water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated under vacuum to dryness. The crude product was purified by chromatographic column on silica gel, eluting with n-hexane/ethylacetate/methanol 12/3/1 (yield: 47%). 1H NMR (CDCl3) δ: 0.91-0.96 (t, 3H, OCH2CH2CH2CH3), 1.39-1.42 (m, 2H, OCH2CH2CH2CH3), 1.65-1.68 (m, 2H, OCH2CH2CH2CH3), 4.17-4.21 (m, 2H, OCH2CH2CH2CH3), 6.48-6.53 (d, 1H, ArCH═CHCO), 7.52-7.54 (m, 1H, benzene H-5), 7.53-7.75 (m, 2H, ArCH═CHCO and benzene H-6), 7.84-7.86 (m, 1H, benzene H-4), 7.99 (m, 1H, benzene H-2), 10.01 (s, 1H, CHO).

後処理

  1. customA 10 mL Schenk tube was dried in oven
  2. customThe Schlenk tube was then sealed under nitrogen
  3. customplaced in a pre-heated oil bath at 140° C.
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum to dryness
  8. customThe crude product was purified by chromatographic column on silica gel

出典と根拠

ORDレコード
ord-0f74b82f2491491bafaa2c19c7ff79e9
出典データセット
uspto-grants-2011_11
特許番号
US08058273B2

反応ノート

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