Reaction #1000

Reaction equation

tetrahydrofuran

sodium borohydride

sodium chloride

2-cycloheptenone ethylene ketal

→

3-hydroxycycloheptanone ethylene ketal

Solvents

sodium hydroxide

sodium hydroxide

water

Conditions

Workup

1. 1
   Otherto give a suspension
2. 2
   Temperaturethe mixture was cooled in an ice water bath
3. 3
   Otherto reach ambient temperature
4. 4
   workup.STIRRINGstirred overnight
5. 5
   workup.STIRRINGstirred for 30 minutes
6. 6
   Otherthe solution was decanted into brine
7. 7
   Extractionextracted with ethyl acetate
8. 8
   Dryingdried over sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated in vacuo

Procedure

Mercury(II) acetate (80.7 g, 0.25 mol) was dissolved in water (150 mL), then tetrahydrofuran (150 mL) was added to give a suspension. To this stirring suspension was added 2-cycloheptenone ethylene ketal (39 g, 0.25 mol). After stirring at ambient temperature for 3 hours, the mixture was cooled in an ice water bath. A 10% aqueous sodium hydroxide solution (150 mL) was added, followed by a solution of sodium borohydride (4.8 g, 0.13 mol) in 10% aqueous sodium hydroxide (150 mL). The mixture was allowed to reach ambient temperature and stirred overnight. The mixture was saturated with sodium chloride, stirred for 30 minutes, then allowed to settle; the solution was decanted into brine and extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo to give 3-hydroxycycloheptanone ethylene ketal (36 g).

Source