Sodium Iodide → hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone

HRID 1722362Notes

Reaction equation

HRID 1722362 reaction equation
[I-].[Na+].C[O:4][CH:5]([CH2:19][CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:17][CH2:16][CH:15]2[CH:11]1[CH2:12][C:13](=[O:18])[CH2:14]2.C[Si](Cl)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[OH:4][CH:5]([CH2:19][CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:17][CH2:16][CH:15]2[CH:11]1[CH2:12][C:13](=[O:18])[CH2:14]2

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24477Sodium ThiosulfateHCID 55994Cioteronel

Product 1

HCID 15053004hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Sodium iodide (3 g) is added to a solution of 1 g of 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} in 20 ml of acetonitrile. The resultant red solution is stirred at room temperature and 2.5 ml of trimethylsilyl chloride is added. After 7.5 hours, water is added, followed by a saturated aqueous sodium thiosulfate solution. The solvent is removed under vacuum, leaving a light yellow oil. Chromatography on silica gel leaves pure 2-(5-hydroxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone}.

Workup

  1. customThe solvent is removed under vacuum
  2. customleaving a light yellow oil

Sources & evidence

ORD record
ord-d76c6f5d14b9478bb896262ffa20a949
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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