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(Trifluoromethyl)trimethylsilane → ethyl 6-methyl-8-(2,2,2-trifluoro-1-hydroxyethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855064
Notes
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Reaction equation

HRID 855064 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH3:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2)=[O:2].C[Si](C)(C)[C:25]([F:28])([F:27])[F:26]>C1COCC1.[F-].C[N+](C)(C)C>[CH3:22][C:5]1[CH:6]=[C:7]2[C:12](=[C:3]([CH:1]([OH:2])[C:25]([F:28])([F:27])[F:26])[CH:4]=1)[O:11][CH:10]([C:13]([F:16])([F:14])[F:15])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 86599485ethyl 8-formyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 86599487ethyl 6-methyl-8-(2,2,2-trifluoro-1-hydroxyethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylateYield 116%

Reagents, catalysts & solvents 2

HCID 67803Tetramethylammonium fluorideCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

The aldehyde from Example 605a, Step 1 (2.0 g, 6.37 mmol) in THF (20 mL) was cooled to 0° C. and treated with 98% trimethyl(trifluoromethyl)silane (1.18 g, 8.28 mmol) and 15 mg tetramethylammonium fluoride. The reaction was allowed to warm to room temperature and stirred for overnight. The HF (48%, 0.24 mL) was added to the reaction and the reaction was stirred for 6 hours. After LCMS indicated that there was no starting material in the reaction, the reaction was quenched with water, extracted with ethyl acetate, washed with water, brine, dried over MgSO4, and concentrated in vacuo to give a yellow semisolid (2.84 g), which had suitable purity to use without further purification.

Workup

  1. additionThe HF (48%, 0.24 mL) was added to the reaction
  2. stirringthe reaction was stirred for 6 hours
  3. customin the reaction
  4. customthe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd1be1d60e2d47369ff2eeafcd3216d2
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259266B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes