Hydrochloric Acid → 1-Benzyl-5-(tert-butyl)dimethylsilyloxy-1-cyclooctanol

HRID 498100Notes

Reaction equation

HRID 498100 reaction equation
[Mg].II.BrCC.[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([CH:19]1[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH:22]([O:28][SiH:29]([CH3:31])[CH3:30])[CH2:21][CH2:20]1)([CH3:18])([CH3:17])[CH3:16].Cl>CCOCC.O>[CH2:7]([C:23]1([OH:27])[CH2:24][CH2:25][CH2:26][CH:19]([C:15]([CH3:17])([CH3:18])[CH3:16])[CH2:20][CH2:21][CH:22]1[O:28][SiH:29]([CH3:30])[CH3:31])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 6332Ethyl BromideHCID 7503Benzyl ChlorideHCID 5462224MagnesiumHCID 1317251665-(Tert-butyl)dimethylsilyloxy-1-cyclooctanone

Product 1

HCID 1317251671-Benzyl-5-(tert-butyl)dimethylsilyloxy-1-cyclooctanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

1.2 g of magnesium was suspended in 40 ml of anhydrous ether, and the resulting suspension was warmed in the water bath at 40° C. A small piece of iodine crystal and a drop of bromoethane were added to the solution, followed by adding 5.7 ml of benzyl chloride dropwise slowly. To the resulting grayish white mixture, 4.0 g of the above product (a) was added. The resulting solution was stirred at 40° C. for three hours followed by at room temperature for further two days. The reaction solution was poured into ice water, and 2N hydrochloric acid was added to the solution until pH of the aqueous phase was reached at approximately 3. Then, the reaction solution was extracted with ether. The organic layer was washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude product was purified by column chromatography on silica gel, and the eluate with ethyl acetate-hexane (1:15) was collected, to afford 4.5 g of the titled compound (b) (mixture of cis- and trans-isoforms) as colorless liquid.

Workup

  1. waitfollowed by at room temperature for further two days
  2. additionwas added to the solution until pH of the aqueous phase
  3. extractionThen, the reaction solution was extracted with ether
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe resulting crude product was purified by column chromatography on silica gel
  8. customthe eluate with ethyl acetate-hexane (1:15) was collected

Sources & evidence

ORD record
ord-6bc922212569474088b9abf6ba8f9bb2
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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