Hydrochloric Acid → HCID 14163612, compound

HRID 2059356Notes

Reaction equation

HRID 2059356 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:5]=1/[CH:18]=[CH:19]/[CH:20]([OH:29])[CH2:21][C:22](=[O:28])[CH2:23][C:24]([O:26][CH3:27])=[O:25].Cl>C(O)C.O>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[C:5]=1/[CH:18]=[CH:19]/[CH:20]([OH:29])[CH2:21][CH:22]([OH:28])[CH2:23][C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 14163608HCID 14163608, compound

Product 1

HCID 14163612HCID 14163612, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium tetrahydridoborate (1.55 g, 41.1 mmole) is added with stirring to a cooled solution (5° C.) of methyl (E)-7-(2,4-dichloro-6-(4-fluorophenyl)phenyl)-5-hydroxy-3-oxo-6-heptenoate (82.3 mmole) in ethanol (200 ml) at a rate sufficient to maintain the internal temperature at 15°-20° C. The resulting solution is stirred with ice-bath cooling for 15 min. and then acidified with 6 N hydrochloric acid. The resulting mixture is diluted with water (500 ml) and extracted with ether (3×250 ml). The organic extracts are combined, washed with brine (4×100 ml), dried over magnesium sulfate and filtered. The filtrate is evaporated in vacuo, leaving the title compound as an oil.

Workup

  1. temperatureto maintain the internal temperature at 15°-20° C
  2. temperaturecooling for 15 min.
  3. extractionextracted with ether (3×250 ml)
  4. washwashed with brine (4×100 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-65df158c298247a78f3bc5c03f65faed
Source dataset
uspto-grants-1982_03
Patent number
US04322563

Reaction notes

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