Sodium Carbonate → 3-Hydroxy-5-[(1E)-3-(methyloxy)-1-propen-1-yl]benzaldehyde

HRID 658237ノート

反応式

HRID 658237 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].[CH3:11][O:12][CH2:13]/[CH:14]=[CH:15]/B1OC(C)(C)C(C)(C)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2](/[CH:15]=[CH:14]/[CH2:13][O:12][CH3:11])[CH:9]=1)[CH:5]=[O:6]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 166410843-Bromo-5-hydroxybenzaldehyde

生成物 1

HCID 574568653-Hydroxy-5-[(1E)-3-(methyloxy)-1-propen-1-yl]benzaldehyde

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

3-Bromo-5-hydroxybenzaldehyde (1 eq.) from the previous step and 2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.) were combined in DMF (0.05 M). To this solution was then added palladium acetate (10 mol %), triphenylphosphine (20 mol %), and sodium carbonate (2 M aqueous solution, 4 eq.). The resulting suspension was heated at 80° C. and stirred for 16 h. The reaction mixture was quenched with 10% aqueous HCl and extracted with ether. The combined organic extracts were washed with water, saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20%→4.33% EtOAc/Hex) to afford the title compound as a yellow oil.

後処理

  1. customThe reaction mixture was quenched with 10% aqueous HCl
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed with water, saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (SiO2, 20%→4.33% EtOAc/Hex)

出典と根拠

ORDレコード
ord-c57e83cbf1824c0eaa72cee3247be9f2
出典データセット
uspto-grants-2011_12
特許番号
US08076359B2

反応ノート

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