Sodium Carbonate → Methyl 3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzoate

HRID 658248

反応式

HRID 658248 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Br)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][O:14][CH2:15]/[CH:16]=[CH:17]/B1OC(C)(C)C(C)(C)O1.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:32]=CC=C[CH:28]=1.[C:46](=O)([O-])[O-:47].[Na+].[Na+]>CN(C=O)C.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:46][O:47][CH2:28]/[CH:27]=[CH:32]/[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](/[CH:17]=[CH:16]/[CH2:15][O:14][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 621923Methyl 3,5-DibromobenzoateHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 57456870Methyl 3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzoate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of methyl 3,5-dibromobenzoate (1 eq.) from the previous step in DMF (0.2 M) was added 2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.1 eq.), palladium acetate (10 mol %), triphenylphosphine (30 mol %), and 2.0 M aqueous sodium carbonate solution (5 eq.). The reaction was heated to 80° C. and stirred for 3 h. After cooling to rt, the reaction was diluted with ether. The organic extract was washed with water, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex) to afford the title compound as an oil.

後処理

  1. temperatureAfter cooling to rt
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex)

出典と根拠

ORDレコード
ord-d53dca1151d34266a90db378e16b3d56
出典データセット
uspto-grants-2011_12
特許番号
US08076359B2

関連ノート

読み込み中…