Hydrochloric Acid → HCID 21279128, compound

HRID 2291635Notes

Reaction equation

HRID 2291635 reaction equation
[CH3:1][O:2][C:3]1[C:7](=[O:8])[O:6][CH:5]([CH2:9][CH2:10][C:11](O)=[O:12])[C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.ClC(OCC(C)C)=O.[BH4-].[Na+].Cl>O1CCCC1.O.C(N(CC)CC)C>[OH:12][CH2:11][CH2:10][CH2:9][CH:5]1[O:6][C:7](=[O:8])[C:3]([O:2][CH3:1])=[C:4]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 13832260HCID 13832260, compound

Product 1

HCID 21279128HCID 21279128, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(4-methoxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionic acid (3 g) and triethylamine (1.95 ml) in tetrahydrofuran was added dropwise iso-butyl chloroformate (1.79 ml) at -20° C. with stirring and the mixture was stirred for 40 minutes at the same temperature. To this mixture was added sodium borohydride (1.11 g) at -20° C. and the mixture was stirred for 3 hours at ambient temperature. After being acidified with 10% hydrochloric acid at 0° , the solvent was removed under the reduced pressure to give a residue which was poured into water and extracted with diethyl ether. The ethereal extract was washed with lN hydrochloric acid and saturated aqueous solution of sodium bicarbonate successively and dried. Evaporation of the solvent gave an oil which was chromatographed on silica gel in chloroform to give 5-(3-hydroxypropyl)-3-methoxy-4- phenyl-2(5H)-furanone (2.35 g) as an oil.

Workup

  1. stirringthe mixture was stirred for 40 minutes at the same temperature
  2. stirringthe mixture was stirred for 3 hours at ambient temperature
  3. customthe solvent was removed under the reduced pressure
  4. customto give a residue which
  5. extractionextracted with diethyl ether
  6. extractionThe ethereal extract
  7. washwas washed with lN hydrochloric acid and saturated aqueous solution of sodium bicarbonate successively
  8. customdried
  9. customEvaporation of the solvent
  10. customgave an oil which
  11. customwas chromatographed on silica gel in chloroform

Sources & evidence

ORD record
ord-185790ce5da142c28ddd3f137bfb416b
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

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