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

HRID 658237노트

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HRID 658237 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c57e83cbf1824c0eaa72cee3247be9f2
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076359B2

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