Chlorotrimethylsilane → HCID 178455792, compound

HRID 1674441Notes

Reaction equation

HRID 1674441 reaction equation
[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)=[CH2:2].[CH3:12][Si](Cl)(C)C>CO>[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1)=[CH2:2]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 178455789HCID 178455789, compound

Product 1

HCID 178455792HCID 178455792, compoundYield 19,050.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

23.0 g of trans-4-vinylcyclohexane carboxylic acid was dissolved in 120 mL of methanol, and added with 0.1 g of trimethylsilylchloride, which was then subjected to reflux for 6 hours. Then, the resultant product was cooled to room temperature and concentrated under reduced pressure. 150 mL of hexane was added thereto, and the methanol phase was separated. Then, the methanol phase was extracted with hexane, and the organic layers were combined and washed with saturated saline. The resultant product was dried over anhydrous sodium sulfate, and then concentrated, to obtain 29.5 g of methyl trans-4-vinylcyclohexane carboxylate in the form of an oil-like product.

Workup

  1. temperatureto reflux for 6 hours
  2. concentrationconcentrated under reduced pressure
  3. addition150 mL of hexane was added
  4. customthe methanol phase was separated
  5. extractionThen, the methanol phase was extracted with hexane
  6. washwashed with saturated saline
  7. dry with materialThe resultant product was dried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-989249d240dc4d2ba45c4bfa2b6bf4ce
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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