Methanol → HCID 18696705, compound

HRID 1870649Notes

Reaction equation

HRID 1870649 reaction equation
[Na].C(OCC)(=O)[CH2:3][C:4](OCC)=[O:5].[Cl:13][C:14]1[C:15]([CH3:31])=[C:16]2[C:20](=[C:21]([CH3:28])[C:22]=1[CH:23]=[CH:24][C:25](=[O:27])[CH3:26])[CH2:19][C:18]([CH3:30])([CH3:29])[CH2:17]2.[CH3:32]O>>[Cl:13][C:14]1[C:22]([CH:23]2[CH2:3][C:4](=[O:5])[CH2:26][C:25](=[O:27])[CH2:24]2)=[C:21]([CH3:28])[C:20]([CH3:19])=[C:16]2[C:15]=1[CH2:31][C:18]([CH2:30][CH3:32])([CH3:29])[CH2:17]2

Participants

5

Reactant 4

HCID 887Methanol2×HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 53978158HCID 53978158, compound

Product 1

HCID 18696705HCID 18696705, compoundYield 87%

Procedure

To a solution of 1.53 g of sodium in 100 ml of absolute methanol was added 10 ml of diethyl malonate, and then the reaction mixture was added 12.65 g of 4-(5-chloro-2,2,4,7-tetramethylindan-6-yl)-3-buten-2-one in 50 ml of absolute methanol. After refluxing for 4 hours, the reaction mixture was evaporated under reduced pressure and then added 70 g of 10% aqueous solution of NaOH. After refluxing for 4 hours, the reaction mixture was cooled to room temperature and washed twice with diethyl ether. Concentrated hydrochloric acid was added dropwise into the boiling aqueous layers until the bubble of gas ceased and then the reaction mixture was cooled to room temperature. Solid produce was collected and dried to afford 11.9 g of the titile compound as yellow solid.

Workup

  1. temperatureAfter refluxing for 4 hours
  2. customthe reaction mixture was evaporated under reduced pressure
  3. additionadded 70 g of 10% aqueous solution of NaOH
  4. temperatureAfter refluxing for 4 hours
  5. washwashed twice with diethyl ether
  6. additionConcentrated hydrochloric acid was added dropwise into the boiling aqueous layers until the
  7. custombubble of gas
  8. temperaturethe reaction mixture was cooled to room temperature
  9. customSolid produce
  10. customwas collected
  11. customdried

Sources & evidence

ORD record
ord-4e5bcfb032364682bfbe2ce502848080
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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