Methanol → HCID 77231251、化合物

HRID 1187084ノート

反応式

HRID 1187084 の反応式
[CH2:1]([C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7](O)=[C:8]([CH:11]=1)[CH:9]=[O:10])[CH:2]=[CH2:3].C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.CCN(CC)CC.CN([CH:46]=[O:47])C.[CH3:48][OH:49]>ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:1]([C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7]([C:48]([O:47][CH3:46])=[O:49])=[C:8]([CH:9]=[O:10])[CH:11]=1)[CH:2]=[CH2:3]

参加物

8

反応物 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471Triethylamine2 回HCID 142176Phenyl triflimideHCID 17138875-Allyl-2-hydroxy-3-methoxybenzaldehyde

生成物 1

HCID 77231251HCID 77231251、化合物

試薬・触媒・溶媒 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a flask containing 5-allyl-2-hydroxy-3-methoxybenzaldehyde (5.0 g, 26.0 mmol) and N-phenyl-trifluoromethanesulfonimide was added DCM (75 mL). The flask was placed at 0° C. and treated with Et3N (4 mL) and stirred for 2 days at room temp. The mixture was diluted with dichloromethane and washed with 1N HCl, saturated sodium bicarbonate solution, and brine, then dried (Na2SO4) and concentrated. The residue in a flask was treated with dppf (0.18 g, 0.45 mmol), PdOAc2 (0.1 g, 0.44 mmol), and Et3N (8 mL, 56 mmol) followed by addition of DMF (45 mL) and MeOH (30 mL). The reaction mixture was then degassed and purged with CO 3 times and stirred under CO for 6 h at 70° C. When LC indicated consumption of starting material, the solution was concentrated to dryness. The organic residue was purified by MPLC (hexanes/EtOAc=1/0.2) to provide methyl 4-allyl-2-formyl-6-methoxybenzoate.

後処理

  1. customwas placed at 0° C.
  2. washwashed with 1N HCl, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe reaction mixture was then degassed
  6. custompurged with CO 3 times
  7. stirringstirred under CO for 6 h at 70° C
  8. customconsumption of starting material
  9. concentrationthe solution was concentrated to dryness
  10. customThe organic residue was purified by MPLC (hexanes/EtOAc=1/0.2)

出典と根拠

ORDレコード
ord-459d7c29f3eb431e9b4a710ade36cf60
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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