Sodium borohydride → HCID 14127272, compound

HRID 728531Notes

Reaction equation

HRID 728531 reaction equation
[Cl:1][C:2]1([Cl:11])[C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH:7]=[CH:8]2)[C:3]1=[O:10].[BH4-].[Na+]>CO>[Cl:1][C:2]1([Cl:11])[C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH:7]=[CH:8]2)[C@H:3]1[OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12507348HCID 12507348, compound2×

Product 1

HCID 14127272HCID 14127272, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3.0 g of (1S,6R)-8,8-dichlorobicyclo [4.2.0]oct-2-en-7-one, the compound of formula (4), is dissolved in 120 ml of methanol and treated at 0° C. with 1.2 g of sodium borohydride, and the mixture is stirred at 25° C. for 1 hour. The solvent is removed under reduced pressure and the residue partitioned between methylene chloride and water. The extract is dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure. The residue is recrystallized from hexane to give (1S,6R,7R)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-ol, [α]D =+214.4° (CHCl3).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue partitioned between methylene chloride and water
  3. dry with materialThe extract is dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-dac26307a020400b9acdce72bb4f5354
Source dataset
uspto-grants-1991_09
Patent number
US05049497

Reaction notes

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