Oct-6-en-2-one → HCID 14127272, compound

HRID 648673Notes

Reaction equation

HRID 648673 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].CC=CCCCC(=O)C.[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

5

Reactant 3

HCID 537566Oct-6-en-2-oneHCID 4311764Sodium borohydrideHCID 12507348HCID 12507348, compound

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 (XXXIX), prepared as shown in Preparation 22, 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°, (C=0.5, CHCl3).

Workup

  1. customas shown in Preparation 22
  2. customThe solvent is removed under reduced pressure
  3. customthe residue partitioned between methylene chloride and water
  4. dry with materialThe extract is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-fcc84f36fa394e96951eb8e2141f5e49
Source dataset
uspto-grants-1988_04
Patent number
US04735966

Reaction notes

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