Dimethylformamide → HCID 59749608, compound

HRID 747382Notes

Reaction equation

HRID 747382 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH2:10][CH2:11][O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[O:16][CH3:17].[Li]CCCC.CN(C)[CH:25]=[O:26]>C1COCC1.O>[CH3:17][O:16][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[CH:25]=[O:26]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 59749610HCID 59749610, compoundHCID 178418339Butyllithium

Product 1

HCID 59749608HCID 59749608, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In a round bottom flask, 1-bromo-2,5-dimethoxy-4-(2-methoxymethoxy-ethyl)-benzene (0.55 g, 18.02 mmol) was dissolved in 30 mL of dry THF. The reaction mixture was cooled to −78° C. using a dry ice-acetone bath and stirred for 10 min. A solution of n-BuLi (0.86 mL of 2.5 M solution in hexane) was added and the reaction mixture was stirred for an additional 30 min. Dimethyl formamide (0.26 g, 36.06 mmol) was added and then the temperature was allowed warm up slowly to room temperature and stirred for 30 min. The reaction mixture was diluted with water and the organic material was extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated in vacuo. The crude material was purified by flash column chromatography using a hexane and ethyl acetate gradient to give colorless oil in 56% yield. MS (m/z) 255 (M+1)+. 1HNMR(CDCl3): δ ppm 2.96 (m, 2H), 3.32 (m, 3H), 3.75 (m, 2H), 3.79 (s, 3H), 4.13 (s, 3H), 4.63 (s, 2H), 6.98 (s, 1H), 7.26 (s, 1H), 10.40 (s, 1H).

Workup

  1. stirringthe reaction mixture was stirred for an additional 30 min
  2. temperaturethe temperature was allowed warm up slowly to room temperature
  3. stirringstirred for 30 min
  4. extractionthe organic material was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe crude material was purified by flash column chromatography
  8. customto give colorless oil in 56% yield

Sources & evidence

ORD record
ord-cf5964d9e3364d81a10612f9aa501ce6
Source dataset
uspto-grants-2008_07
Patent number
US07396856B2

Reaction notes

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