Triethylamine → tert-butyl (2E)-3-[2-(hydroxymethyl)-4-methylphenyl]acrylate

HRID 64421ノート

反応式

HRID 64421 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][OH:10].[C:11]([O:15][C:16](=[O:19])[CH:17]=[CH2:18])([CH3:14])([CH3:13])[CH3:12].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C(OCC)(=O)C.O.CN(C=O)C>[OH:10][CH2:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1/[CH:18]=[CH:17]/[C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:19]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 54173415(2-Bromo-5-methylphenyl)methanol

生成物 1

HCID 86713430tert-butyl (2E)-3-[2-(hydroxymethyl)-4-methylphenyl]acrylate

試薬・触媒・溶媒 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2.64 g of (2-bromo-5-methylphenyl)methanol, 246 mg of bis(dibenzylideneacetone)palladium, 2.95 ml of tert-butylacrylate, 442 mg of tris(2-methylphenyl)phosphine, 2.5 ml of triethylamine, and 24 ml of DMF was stirred at 100° C. for 24 hours. After leaving to be cooled at room temperature, water and ethyl acetate were added thereto to carry out a layer separation operation. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.32 g of tert-butyl (2E)-3-[2-(hydroxymethyl)-4-methylphenyl]acrylate.

後処理

  1. customAfter leaving
  2. temperatureto be cooled at room temperature
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-889565f5456a4cd5a1a167f7cafd3cb8
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

反応ノート

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