Dimethylformamide → 2-(Dimethylamino)-3-methylbenzaldehyde

HRID 215930노트

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HRID 215930 반응식
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]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8003PentaneHCID 58006241HCID 58006241, 화합물HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 130217582-(Dimethylamino)-3-methylbenzaldehyde

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9def0dcc01c49aeb9e729b45933fda2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193203B2

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