Dimethylformamide → HCID 86593857, compound

HRID 268582Notes

Reaction equation

HRID 268582 reaction equation
CN(CCN(C)C)C.[CH3:9][C:10]([CH3:28])([CH3:27])[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:15]=1.[Li]CCCC.CN([CH:37]=[O:38])C>CCOCC>[CH3:9][C:10]([CH3:28])([CH3:27])[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:15]=1[CH:37]=[O:38]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 69310955HCID 69310955, compoundHCID 178418339Butyllithium

Product 1

HCID 86593857HCID 86593857, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

TMEDA (23.0 g, 0.198 mol), 1,3-di(3,3-dimethylbutoxy)benzene (46.2 g, 0.166 mol) and ether (500 mL) were brought together in a two-neck 1-L flask fitted with a nitrogen inlet and a pressure-equalizing addition funnel. The reaction mixture was cooled to 0° C., and deaerated. n-BuLi (2.5 M solution in hexanes, 0.18 mol) was added dropwise over a period of 30 min via the addition funnel. The mixture was stirred for 3 h, following which that time it was warmed to room temperature. At this point DMF (23.0 g, 0.315 mol) was added dropwise; after 2 h of stirring, the reaction was quenched with water, extracted with ether (4×300 mL), separated, and evaporated. The product was purified by chromatography on silica using 9:1 hexanes:ethyl acetate as the eluant, giving 36.6 g of product (72% yield, based on 46.2 g of the 1,3-di(3,3-dimethylbutoxy)benzene starting material). 1H NMR (250 MHz, CDCl3): 10.49 (s, 1H), 7.37 (t, 1H, J=8.5 Hz), 6.52 (d, 2H, J=8.5 Hz), 4.06 (t, 4H, J=7.2 Hz), 1.76 (t, 4H, J=7.2 Hz), 0.96 (s, 18H). HRMS (ESI+) m/z: 329.2107 (calcd for C19H30O3Na (M+Na)+ 329.2092).

Workup

  1. temperaturewas warmed to room temperature
  2. stirringafter 2 h of stirring
  3. customthe reaction was quenched with water
  4. extractionextracted with ether (4×300 mL)
  5. customseparated
  6. customevaporated
  7. customThe product was purified by chromatography on silica using 9:1 hexanes

Sources & evidence

ORD record
ord-2e8442a9e4d74eb4a9187ceac3c4bb29
Source dataset
uspto-grants-2008_11
Patent number
US07445845B2

Reaction notes

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