(Trifluoromethyl)trimethylsilane → HCID 59463781, compound

HRID 1713347Notes

Reaction equation

HRID 1713347 reaction equation
[CH3:1][C:2]1([CH2:14][CH:15]=[O:16])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=2)[O:5][CH2:4][CH2:3]1.C[Si](C)(C)[C:19]([F:22])([F:21])[F:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:20][C:19]([F:22])([F:21])[CH:15]([OH:16])[CH2:14][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride2×HCID 59463783HCID 59463783, compound

Product 1

HCID 59463781HCID 59463781, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 383 mg (1.6 mmol) of (4-methyl-6-methylsulfanylchroman-4-yl)acetaldehyde and 0.335 mL (1.4 mmol) of trimethyl(trifluoromethyl)silane in 5 mL of tetrahydrofuran was added 3 drops of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran. The mixture stirred for 1 hour and then an additional 1.8 mL (1.8 mmol) of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran was added. After 18 hours, the mixture was concentrated in vacuo and diluted with 1N aqueous HCl and extracted with three 50 mL portions of diethyl ether. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 0.45 g of 1,1,1-trifluoro-3-(4-methyl-6-methylsulfanylchroman-4-yl)propan-2-ol as a mixture of diastereomers. The crude oil was used without further purification.

Workup

  1. waitAfter 18 hours
  2. concentrationthe mixture was concentrated in vacuo
  3. additiondiluted with 1N aqueous HCl
  4. extractionextracted with three 50 mL portions of diethyl ether
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb56bf71c56e49fa9324764b9cab23bc
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

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