Hydrochloric Acid → HCID 15332544, compound

HRID 1440993Notes

Reaction equation

HRID 1440993 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[CH3:11][Si:12]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>O1CCCC1>[O:4]=[C:2]([CH:15]([CH2:14][CH2:13][Si:12]([CH3:21])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:11])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:1]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 15332486HCID 15332486, compound

Product 1

HCID 15332544HCID 15332544, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flask under a nitrogen atmosphere were placed 1.7 g (0.075 mole) metallic sodium and 75 mL of absolute ethanol. When all of the sodium had reacted, the remaining ethanol was evaporated, leaving solid sodium ethoxide. To this solid were added successively 100 mL of dry tetrahydrofuran, 11.0 g (0.075 mole) of diethyl oxalate, and 12.95 g (0.0517 mole) of ethyl 5-methyl-5-phenyl-5-silahexanoate. This mixture was heated at reflux for one hour after which it was cooled to ambient temperature before being poured into 240 mL of 0.5N hydrochloric acid. This mixture was extracted with 200 mL of diethyl ether. The extract was evaporated under reduced pressure, leaving 16.7 g of diethyl 2-oxo-3-(3-methyl-3-phenyl-3-silabutyl)succinate as an oil. This reaction was repeated to provide additional product for subsequent steps in this synthesis.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for one hour after which it
  3. extractionThis mixture was extracted with 200 mL of diethyl ether
  4. customThe extract was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c87882a72e2d4efba2bd3570d59a1342
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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