Dimethylformamide → HCID 10932755, compound

HRID 1042521Notes

Reaction equation

HRID 1042521 reaction equation
CN(CCN(C)C)C.[Li]CCCC.[C:14]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN([CH:31]=[O:32])C>C1COCC1>[CH3:27][O:26][C:21]1[C:22]([CH:31]=[O:32])=[CH:23][CH:24]=[CH:25][C:20]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 68352-MethoxybiphenylHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 178418339Butyllithium

Product 1

HCID 10932755HCID 10932755, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 17.4 g (0.15 mol) of dry TMEDA in 600 mL of hexanes, 60.0 mL (0.15 mol) of 2.5 M nBuLi in hexanes was added at room temperature. This mixture was stirred for 30 min, and then 27.6 g (0.15 mol) of 2-phenylanisol was added. This mixture was stirred for 4 hr at 55° C., then heated to 100° C., and a solution of 28.0 g (0.38 mol) of DMF in 200 mL of THF was added dropwise with vigorous stirring. The resulting mixture was evaporated to dryness, and the product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-diethyl ether from 100:1 to 20:1, vol.) to yield 26.1 g (82%) of the title product.

Workup

  1. stirringThis mixture was stirred for 4 hr at 55° C.
  2. customThe resulting mixture was evaporated to dryness
  3. customthe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-diethyl ether from 100:1 to 20:1, vol.)

Sources & evidence

ORD record
ord-de26e7ac65664808b80bad9b887a0244
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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