Dimethylformamide → HCID 19010432, compound

HRID 1741587Notes

Reaction equation

HRID 1741587 reaction equation
[H-].[Na+].CN(C=O)C.[OH:8][CH2:9][CH:10]1[S:15][C:14]2[S:16][CH:17]=[CH:18][C:13]=2[CH:12]([O:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[CH2:11]1.[CH3:26][O:27][CH2:28][CH2:29]Br>O>[CH3:26][O:27][CH2:28][CH2:29][O:8][CH2:9][CH:10]1[S:15][C:14]2[S:16][CH:17]=[CH:18][C:13]=2[CH:12]([O:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[CH2:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 131718630HCID 131718630, compound

Product 1

HCID 19010432HCID 19010432, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under N2, a suspension of 60% NaH (20 g, 0.5 mol), DMF (350 ml) and 7 (38.3 g, 0.13 mol) was stirred at ambient temperature. After 2.5 h. the reaction was cooled to 0°-4° C. and 2-methoxyethylbromide (71 g, 0.51 mol) was added dropwise. After complete addition, the reaction was allowed to stir to room temperature overnight. The solution was then poured into H2O and the aqueous layer was extracted with EtOAc (3x). The organic layer was washed with saturated NaCl, dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column with silica gel and the product eluted with 20% EtOAc-hexane to yield 39 g (84%) of 8.

Workup

  1. temperatureAfter 2.5 h. the reaction was cooled to 0°-4° C.
  2. additionAfter complete addition
  3. stirringto stir to room temperature overnight
  4. extractionthe aqueous layer was extracted with EtOAc (3x)
  5. washThe organic layer was washed with saturated NaCl
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was chromatographed on a Still column with silica gel
  10. washthe product eluted with 20% EtOAc-hexane

Sources & evidence

ORD record
ord-32b1fec22338436db1191c45b5129864
Source dataset
uspto-grants-1994_08
Patent number
US05334591

Reaction notes

Loading…