Sulfuric Acid → HCID 20286772, compound

HRID 1413124Notes

Reaction equation

HRID 1413124 reaction equation
[BH4-].[Na+].[OH:3][CH:4]([CH:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:15])[CH2:5][C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].S(=O)(=O)(O)O>C(O)C>[OH:13][CH:6]([CH2:5][CH:4]([OH:3])[CH:14]([O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:15])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 20286762HCID 20286762, compound

Product 1

HCID 20286772HCID 20286772, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 2.5 g (0.006 mole) sodium borohydride in 30 ml of absolute ethanol was added dropwise 30 ml of an absolute ethanol solution containing 3.5 g 80.0135 mole) of the ethyl 5-hydroxy-3-oxo-6-phenoxyheptanoate obtained in step (a). After completion of the addition, cooling was immediately stopped and the mixture was allowed to warm to room temperature and was stirred for about 40 minutes. To the reaction mixture were then added about 300 ml of ice-water and the mixture was then acidified by the addition of 2 N sulphuric acid. After saturating the solution with sodium chloride, it was extracted three times, each time with 50 ml of ethyl acetate. The combined extracts were dried over anhydrous sodium sulphate and then the solvent was evaporated off, to give 1.3 g (yield 37%) of ethyl 3,5-dihydroxy-6-phenoxyheptanoate.

Workup

  1. additionAfter completion of the addition
  2. temperaturecooling
  3. concentrationAfter saturating the solution with sodium chloride, it
  4. extractionwas extracted three times
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulphate
  6. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-30ccba9e46d64a2d89e98cd9237ce6e1
Source dataset
uspto-grants-1981_02
Patent number
US04248889

Reaction notes

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