Sodium Bicarbonate → HCID 13251517, compound

HRID 905126Notes

Reaction equation

HRID 905126 reaction equation
[CH3:1][O:2][CH:3](Cl)[CH:4]([C:10]([Cl:13])([CH3:12])[CH3:11])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[C:15](=O)(O)[O-:16].[Na+]>CO>[Cl:13][C:10]([CH3:12])([CH3:11])[CH:4]([CH:3]([O:16][CH3:15])[O:2][CH3:1])[CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20253180HCID 20253180, compound

Product 1

HCID 13251517HCID 13251517, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of Step A of Example 1 was added to methanol at a low temperature and the mixture was stirred at 5°-10° C. for 3 hours and was poured into aqueous sodium bicarbonate solution. The mixture was filtered and the decanted aqueous phase was extracted with methylene chloride. The organic phase was washed with aqueous sodium bicarbonate solution and evaporated to dryness under reduced pressure to obtan 11 g of residue. The latter was chromatographed over silica gel and was eluted with a 9-1 petroleum ether (b.p.=40°-70° C.)-ethyl acetate mixture to obtain 8.66 g of methyl 4-chloro-4-methyl-3-dimethoxymethyl-pentanoate with a boiling point of 62° C. at 0.05 mm Hg which was identical to the product of Step A of Example 3.

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe decanted aqueous phase was extracted with methylene chloride
  3. washThe organic phase was washed with aqueous sodium bicarbonate solution
  4. customevaporated to dryness under reduced pressure
  5. customThe latter was chromatographed over silica gel
  6. washwas eluted with a 9-1 petroleum ether (b.p.=40°-70° C.)-ethyl acetate mixture

Sources & evidence

ORD record
ord-35f13cf2e85248bbac398a57635e8dbe
Source dataset
uspto-grants-1983_12
Patent number
US04421928

Reaction notes

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