Water → 6-Methoxy-1-methyl-1-(trifluoromethyl)-1,4-dihydro-3H-2-benzopyran-3-one

HRID 1019365Notes

Reaction equation

HRID 1019365 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13]([CH3:23])(O[Si](C)(C)C)[C:14]([F:17])([F:16])[F:15].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:12][O:11][C:9]1[CH:10]=[C:5]2[C:6](=[CH:7][CH:8]=1)[C:13]([CH3:23])([C:14]([F:15])([F:16])[F:17])[O:24][C:3](=[O:2])[CH2:4]2

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59921414HCID 59921414, compound

Product 1

HCID 184010256-Methoxy-1-methyl-1-(trifluoromethyl)-1,4-dihydro-3H-2-benzopyran-3-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the crude reaction mixture described in example 8 containing a solution of [5-methoxy-2-(2,2,2-trifluoro-1-methyl-1-trimethylsilanyloxy-ethyl)-phenyl]-acetic acid methyl ester was added tetrabutylammonium fluoride (9.00 mL of a 1.0M solution in tetrahydrofuran, 9.00 mmol). The reaction mixture was stirred for 1 hour after which it was poured into water (50 mL) and extracted with methyl tert-butyl ether (50 mL). The organic layer was washed with water (50 mL) and brine (30 mL), dried over magnesium sulfate, filtered, and concentrated to afford 6-methoxy-1-methyl-1-trifluoromethyl-isochroman-3-one as an oil (1.26 g, 54%). 1H NMR (400 MHz, CDCl3) δ1.89 (s, 3), 3.71 (d, 1, J=20.6), 3.79 (s, 3), 3.89 (d, 20.8), 6.65 (d, 1, J=1.5), 6.85-6.89 (m, 1), 7.29 (d, 1, J=8.7). 13C NMR (100 MHz, CDCl3) δ21.45, 34.32, 55.33, 83.01 (q, J=30.3), 112.21, 113.88, 120.57, 124.68 (q, J=285.7), 127.73, 132.18, 160.75, 167.45. IR 1765, 1614, 1509, 1322, 1301, 1274, 1259, 1183, 1101, 997, 813 cm−1. Analysis calculated for C12H11F3O3: C, 55.39; H, 4.26. Found: C, 55.03; H, 4.54.

Workup

  1. customTo the crude reaction mixture
  2. extractionextracted with methyl tert-butyl ether (50 mL)
  3. washThe organic layer was washed with water (50 mL) and brine (30 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-920dc330c30f4daaa48c6c2666fe1ada
Source dataset
uspto-grants-2002_11
Patent number
US06486325B1

Reaction notes

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