(Trifluoromethyl)trimethylsilane → HCID 57809779, compound

HRID 1713335Notes

Reaction equation

HRID 1713335 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2([CH2:13][CH:14]=[O:15])[CH3:12].C[Si](C)(C)[C:18]([F:21])([F:20])[F:19].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:19][C:18]([F:21])([F:20])[CH:14]([OH:15])[CH2:13][C:5]1([CH3:12])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride2×HCID 57809946HCID 57809946, compound

Product 1

HCID 57809779HCID 57809779, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 1.7 g (8.16 mmol) of (6-fluoro-4-methylchroman-4-yl)acetaldehyde and 1.69 mL (11.43 mmol) of trimethyl(trifluoromethyl)silane in 15 mL of tetrahydrofuran was added 1 mL (1 mmol) of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran. The mixture stirred for 1 hour and then an additional 9 mL (9 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 1 N 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 2.4 g of crude 1,1,1-trifluoro-3-(6-fluoro-4-methylchroman-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 1 N 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-8d360faa6e854161adbf851b3cfbafce
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

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