(E)-4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobut-2-enoic acid → 4-(3,5-Dibromo-4-hydroxyphenyl)-4-oxobutanoic acid

HRID 2061414ノート

反応式

HRID 2061414 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8]>C(OCC)(=O)C.O.C(OCC)C.Cl.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8]

参加物

7

反応物 1

HCID 59829196(E)-4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobut-2-enoic acid

生成物 1

HCID 45806384-(3,5-Dibromo-4-hydroxyphenyl)-4-oxobutanoic acid収率 36%

試薬・触媒・溶媒 5

HCID 23994Zinc触媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of (E)-4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobut-2-enoic acid (G) (2.852 g, 8.149 mmol) in ethyl acetate (27 mL) and water (3 mL) was added zinc power (5.7 g) portion wise until no further gas evolution was observed. At this point, the reaction mixture was diluted with diethyl ether (50 mL) and HCl (2 M solution, 8 mL) and the resulting mixture was filtered through a pad of Celite. After filtration, the organic solution was washed with HCl (2 M solution, 10 mL), followed by water (3×10 mL). The organic layer was then dried (MgSO4) and concentrated in vacuo to give a brown solid. This was then triturated with cold ethanol to give the title compound as a pale brown solid (1.025 g, 36%). 1H NMR δ (ppm) (DMSO-d6): 2.58 (2 H, t, J=6.12 Hz), 3.17-3.27 (2 H, m), 8.15 (2 H, s), 10.99 (1 H, s), 12.19 (1H, s)

後処理

  1. filtrationthe resulting mixture was filtered through a pad of Celite
  2. filtrationAfter filtration
  3. washthe organic solution was washed with HCl (2 M solution, 10 mL)
  4. dry with materialThe organic layer was then dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a brown solid
  7. customThis was then triturated with cold ethanol

出典と根拠

ORDレコード
ord-4e844d73be424d60a5fbcabd6f4dd706
出典データセット
uspto-grants-2012_10
特許番号
US08283351B2

反応ノート

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