Hydrochloric Acid → HCID 13459165, compound

HRID 374248Notes

Reaction equation

HRID 374248 reaction equation
[CH2:1]([CH:4]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH3:17])=[O:9])[C:5]([O-])=[O:6])[CH:2]=[CH2:3].[BH4-].[Li+].O.Cl>O1CCCC1>[CH2:1]([CH:4]([CH2:5][OH:6])[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH3:17])[OH:9])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 19809578HCID 19809578, compound

Product 1

HCID 13459165HCID 13459165, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-allyl-3-(2-ethylphenyl)-3-oxopropionate (7.3 g.) in dry tetrahydrofuran (THF) (40 ml.) was added during 10 minutes to a stirred suspension of lithium borohydride (1.32 g.) in dry THF (40 ml.) at 0° C. under a nitrogen atmosphere. The mixture was then stirred at room temperature for 18 hours, cooled to 0°-5° C. and water (40 ml.) added. The aqueous mixture was acidified to pH 2 (concentrated hydrochloric acid) and extracted with ethyl acetate (3×120 ml.). The combined extracts were washed with saturated brine, dried (MgSO4) and evaporated. The residual oil (6.1 g.) was purified by chromatography on silica (180 g.) using 3:7 v/v ethyl acetate/petroleum ether (b.p.60°-80° C.) to give 2-allyl-1-(2-ethylphenyl)propane-1,3-diol (containing approximately 4:1 erythro- to threo-forms) as an oil (4.0 g.); NMR: 1.19 (3H,m), 2.04 (5H,m), 2.59 (2H,m), 3.76 (2H,m), 5.02 (3H,m), 5.67 (1H,m), 7.17 (3H,m), and 7.47 (1H,m)ppm.

Workup

  1. temperaturecooled to 0°-5° C.
  2. extractionextracted with ethyl acetate (3×120 ml.)
  3. washThe combined extracts were washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residual oil (6.1 g.) was purified by chromatography on silica (180 g.)

Sources & evidence

ORD record
ord-95ebf72799a84794878954006e090c4e
Source dataset
uspto-grants-1992_11
Patent number
US05166377

Reaction notes

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