Water → HCID 68976166, compound

HRID 657533Notes

Reaction equation

HRID 657533 reaction equation
Br[CH2:2][O:3][C:4]1[C:5]([O:10][CH3:11])=[CH:6][CH:7]=[CH:8][CH:9]=1.[NH2-].[Na+].[CH2:14]([O:16][C:17]([O:19][CH2:20][CH3:21])=[CH2:18])[CH3:15].O>C1(C)C=CC=CC=1>[CH2:14]([O:16][C:17]1([O:19][CH2:20][CH3:21])[C:9]2[C:8](=[CH:7][CH:6]=[C:5]([O:10][CH3:11])[C:4]=2[O:3][CH3:2])[CH2:18]1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24533Sodium amideHCID 1376731,1-DiethoxyetheneHCID 22961196HCID 22961196, compound

Product 1

HCID 68976166HCID 68976166, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-10 °C

Procedure

24 g (107 mmol) of bromoveratrol is poured onto 8.4 g (215 mmol)/2 eq.) of sodium amide in 10 mL of toluene, followed by 25 g (215 mmol/2 eq.) of 1,1diethoxyethylene. Heating is carried out at 80° C. for 4 hours 30 minutes; cooling to −10° C. is carried out and 50 mL of water and then 50 mL of toluene are poured in. The phases are separated and the aqueous phase is extracted again with toluene. The combined toluene phases are washed with water to neutral pH and are then concentrated. The residue is chromatographed over 600 g of silica (eluant: dichloromethane) to yield the desired product.

Workup

  1. temperatureHeating
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted again with toluene
  4. washThe combined toluene phases are washed with water to neutral pH
  5. concentrationare then concentrated
  6. customThe residue is chromatographed over 600 g of silica (eluant: dichloromethane)

Sources & evidence

ORD record
ord-54bf8476b5ce457e9c3e1b49d6a5f8f3
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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