Hydrochloric Acid → Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate

HRID 1386580ノート

反応式

HRID 1386580 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:21]=[CH:20][C:19]([O:23][CH3:24])=[O:22])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH2:17][CH3:18]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 6187094-Bromo-4'-pentylbiphenyl

生成物 1

HCID 54407370Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4-bromo-4′-pentylbiphenyl (5.0 g), methyl acrylate (2.2 ml), palladium acetate (0.11 g) and tris(o-tolyl)phosphine (0.60 g) in triethylamine (16 ml) was refluxed for 15 hours under nitrogen atmosphere. The reaction mixture was poured into a mixture of cold water and ethyl acetate, and adjusted to about pH 1.5 with 6N hydrochloric acid. The separated organic layer was washed in turn with water and brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude powder, which was subjected to column chromatography on silica gel (200 ml), and eluted with a mixture of (n-hexane:ethyl acetate=100:0-94:6, V/V) to give Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate (4.48 g).

後処理

  1. temperaturewas refluxed for 15 hours under nitrogen atmosphere
  2. washThe separated organic layer was washed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customto give a crude powder, which
  7. washeluted with a mixture of (n-hexane:ethyl acetate=100:0-94:6, V/V)

出典と根拠

ORDレコード
ord-f055f41a22674cd1a50d461cc05f6980
出典データセット
uspto-grants-2001_07
特許番号
US06265536B1

反応ノート

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