Hydrochloric Acid → HCID 54410073, compound

HRID 342501Notes

Reaction equation

HRID 342501 reaction equation
[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[CH:11]([C:14]1[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[C:18]([CH:21]=1)[CH2:19]Cl)([CH3:13])[CH3:12].Cl>C1COCC1.CCCCCC>[CH:11]([C:14]1[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[C:18]([CH2:19][CH2:7][C:5](=[O:6])[CH2:4][C:3]([O:9][CH3:10])=[O:8])[CH:21]=1)([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 543944162-(Chloromethyl)-1-methoxy-4-(propan-2-yl)benzene

Product 1

HCID 54410073HCID 54410073, compoundYield 108.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of sodium hydride (60% oil suspension, 0.44 g,11 mmol) in THF (25 ml) was added methyl acetoacetate (1.08 ml, 10 mmol) dropwise at 0° C. After 10 min stirring at 0° C., n-buthyllithium (1.31M in hexane, 8 ml, 10.5 mmol) was added to the reaction mixture at 0° C. To this orange color solution was added a solution of 5-isopropyl-2-methoxybenzyl chloride (1.99 9, 10 mmol) in THF (5 ml) at 0° C. After 40 min stirring at 0° C. to room temperature, the reaction mixture was poured into 1N HCl (20 ml) and extracted with ethyl acetate. The extract combined was dried (MgSO4) and concentrated to give 3.02 g of yellow oil, which was purified by column chromatography on silica gel (hexane/ethyl acetate: 10/1 as eluent) to afford 1.55 g (55.8%) of title compound as yellow oil.

Workup

  1. stirringAfter 40 min stirring at 0° C. to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract combined was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8754d121fd5345f084adb7d4c8e8a8eb
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Reaction notes

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