Hydrochloric Acid → Ethyl 3-(4-biphenylylthio)lactate

HRID 1706410Notes

Reaction equation

HRID 1706410 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([S:7][CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][CH:2]=1.[BH4-].[Na+].O.Cl>C(O)(C)C>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][C:4]([S:7][CH2:8][CH:9]([OH:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 23332069HCID 23332069, compound

Product 1

HCID 23332067Ethyl 3-(4-biphenylylthio)lactateYield 24.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred suspension of ethyl 3-(4-biphenylylthio)-2-oxopropionate (1.44 g, 0.0048 mole) in isopropanol (24 ml) was added sodium borohydride (0.18 g, 0.0048 mole). After 2 hrs., water (75 ml) and 2 N HCl (0.5 ml) were added. The mixture was extracted with methylene chloride (2×150 ml). The contents of the combined extracts, after drying (Na2SO4) and concentration, were chromatographed on silica gel (120 g) using 1,1,1-trichloroethane as eluting solvent to obtain 0.35 g (24%) of ethyl 3-(4-biphenylylthio)lactate, m.p. 101.5°-102° C.

Workup

  1. extractionThe mixture was extracted with methylene chloride (2×150 ml)
  2. customThe contents of the combined extracts, after drying
  3. concentration(Na2SO4) and concentration
  4. customwere chromatographed on silica gel (120 g)
  5. washas eluting solvent

Sources & evidence

ORD record
ord-ebc3d8ed8d0944b9936e9bcae8c14890
Source dataset
uspto-grants-1980_06
Patent number
US04207329

Reaction notes

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