Dimethylformamide → HCID 20095713, compound

HRID 248554Notes

Reaction equation

HRID 248554 reaction equation
Br[C:2]1[C:3]([O:16][CH2:17][CH3:18])=[CH:4][C:5]([O:13][CH2:14][CH3:15])=[C:6]([O:9][CH2:10][O:11][CH3:12])[C:7]=1[CH3:8].CCCCCC.CN(C)[CH:27]=[O:28].[Cl-].[NH4+].C1C[O:35][CH2:34]C1>>[CH2:17]([O:16][C:3]1[C:4]([O:28][CH3:27])=[C:5]([O:13][CH2:14][CH3:15])[C:6]([O:9][CH2:10][O:11][CH3:12])=[C:7]([CH3:8])[C:2]=1[CH:34]=[O:35])[CH3:18]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 20095706HCID 20095706, compound

Product 1

HCID 20095713HCID 20095713, compound

Conditions

Temperature
-40 °C

Procedure

43.6 g of 5-bromo-2,4-diethoxy-6-methyl-1-methoxymethyloxybenzene prepared in Referential Example 8 was dissolved in 220 ml of THF, and 100 ml of n-buthyllithium (1.6 M n-hexane solution) was dropwise added thereto at -70° C. The mixture was stirred at -40° C. for 30 min, and 11.9 g of dimethylformamide was dropwise added thereto. The temperature of the reaction mixture was returned to room temperature, and an aqueous ammonium chloride solution was added thereto,-followed by extracting with ethyl acetate. The organic phase was washed with water, dried, concentrated and purified by silica gel column chromatography (eluent; n-hexane : ethyl acetate=90 : 10) to prepare 19.2 g of the product compound as a colorless oleaginous substance.

Workup

  1. customat -70° C
  2. customwas returned to room temperature
  3. extractionby extracting with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (eluent; n-hexane : ethyl acetate=90 : 10)
  8. customto prepare 19.2 g of the product compound as a colorless oleaginous substance

Sources & evidence

ORD record
ord-9085fcc9bd1e485fb332a0dc44c9ceac
Source dataset
uspto-grants-1993_05
Patent number
US05210239

Reaction notes

Loading…