Triethylamine → 3-(4-Hydroxymethylphenyl)acrylic acid ethyl ester

HRID 2218117ノート

反応式

HRID 2218117 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:36]([O:40][CH2:41][CH3:42])(=[O:39])[CH:37]=[CH2:38]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:41]([O:40][C:36](=[O:39])[CH:37]=[CH:38][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)[CH3:42]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 701194-Bromobenzyl alcohol

生成物 1

HCID 684575823-(4-Hydroxymethylphenyl)acrylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

実験手順

4-Bromobenzyl alcohol (10.5 g, 56.1 mmol), triphenylphosphine (0.5 g, 1.9 mmol) and palladium acetate (0.5 g, 2.2 mmol) were stirred at reflux in ethyl acrylate (20 mL) and triethylamine (100 mL) for 72 hours, then allowed to cool. The reaction mixture was filtered through celite (Diatomaceous Earth), then concentrated. The crude solid was purified by chromatography on silica gel (20% v/v ethyl acetate in petroleum ether) to afford the title compound as an oil.

後処理

  1. temperatureto cool
  2. filtrationThe reaction mixture was filtered through celite (Diatomaceous Earth)
  3. concentrationconcentrated
  4. customThe crude solid was purified by chromatography on silica gel (20% v/v ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-cec32b817e254fb298ae4f7643043384
出典データセット
uspto-grants-2008_08
特許番号
US07410984B2

反応ノート

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