Dimethylformamide → 2-(Dimethylamino)-3-methylbenzaldehyde

HRID 215930ノート

反応式

HRID 215930 の反応式
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[N:4]([CH3:6])[CH3:5].[Li]C(C)(C)C.CCCCC.CN([CH:25]=[O:26])C>CCOCC>[CH3:5][N:4]([CH3:6])[C:3]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:2]=1[CH:25]=[O:26]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8003PentaneHCID 58006241HCID 58006241、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 130217582-(Dimethylamino)-3-methylbenzaldehyde

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

To a solution of Compound 150 (0.17 g, 0.81 mmol) in Et2O (5.0 mL) at −78° C. under Argon atmosphere was added dropwise a solution of 1.7M t-BuLi in pentane (1.0 mL, 1.79 mmol), and the reaction was stirred for 1 h. DMF (0.25 mL, 3.24 mmol) was added, and the cooling bath was removed. After 1h15, the reaction was cooled to 0° C., and saturated NH4Cl was added. The mixture was extracted with EtOAc, washed with brine, dried over MgSO4, and filtered. The solvent was removed, and the residue was purified by silica gel flash chromatography with EtOAc (15%) and hexanes (85%) as eluent to produce Compound 151 as a yellow oil.

後処理

  1. customthe cooling bath was removed
  2. additionsaturated NH4Cl was added
  3. extractionThe mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel flash chromatography with EtOAc (15%) and hexanes (85%) as eluent

出典と根拠

ORDレコード
ord-e9def0dcc01c49aeb9e729b45933fda2
出典データセット
uspto-grants-2012_06
特許番号
US08193203B2

反応ノート

読み込み中…