Sodium borohydride → HCID 11831680, compound

HRID 1589914Notes

Reaction equation

HRID 1589914 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:11]([CH:13]([CH3:15])[CH3:14])=[O:12])=[C:8]([OH:10])[CH:9]=1>C(O)(C)C.C(OC)(C)(C)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:11]([OH:12])[CH:13]([CH3:14])[CH3:15])=[C:8]([OH:10])[CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 10922743HCID 10922743, compound

Product 1

HCID 11831680HCID 11831680, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

40.8 g (1.08 mol) of sodium borohydride are added to 1,100 ml of isopropanol, and 261 g (1.08 mol) of the 5-bromo-2-(1-methylethylcarbonyl)phenol from Example 2, dissolved in 300 ml of isopropanol, are added dropwise. The mixture is subsequently stirred at 80° C. for 2 hours and cooled, the solvent is removed, and the residue obtained is taken up in methyl tert-butyl ether (MTBE) and ice water. The mixture is extracted by shaking, the organic phase is separated off, and the aqueous phase is back-extracted several times with MTBE. The combined organic phases are dried and freed from solvent at 20° C. under reduced pressure. The residue obtained in this way is recrystallized from n-hexane, an optimum yield being obtained by cooling the mixture to -40° C. for crystallization.

Workup

  1. additionare added dropwise
  2. temperaturecooled
  3. customthe solvent is removed
  4. customthe residue obtained
  5. extractionThe mixture is extracted
  6. stirringby shaking
  7. customthe organic phase is separated off
  8. extractionthe aqueous phase is back-extracted several times with MTBE
  9. customThe combined organic phases are dried
  10. customfreed from solvent at 20° C. under reduced pressure
  11. customThe residue obtained in this way
  12. customis recrystallized from n-hexane
  13. customan optimum yield
  14. custombeing obtained
  15. temperatureby cooling the mixture to -40° C.
  16. customfor crystallization

Sources & evidence

ORD record
ord-4cf9e4ed2bed47d5ad35a52efd92c97b
Source dataset
uspto-grants-1993_04
Patent number
US05200532

Reaction notes

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