(Trifluoromethyl)trimethylsilane → HCID 57809779, compound

HRID 2106042Notes

Reaction equation

HRID 2106042 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 (11.4 mmol) of trimethyl(trifluoromethyl)silane in 15 mL of tetrahydrofuran was added 1 mL (1 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran. The mixture stirred for 1 hour and then an additional 9 mL (9 mmol) of a 1M 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 and concentrated in vacuo to afford 2.4 g of crude 1,1,1-trifluoro-3-(6-fluoro-4-methylchroman4-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. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55f1c2fa963540a6aa435b0ea167ecd4
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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