Trifluoroacetic acid → 6-Methoxy-1-methyl-1-trifluoromethylisochroman

HRID 1019367Notes

Reaction equation

HRID 1019367 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:17])([C:13]([F:16])([F:15])[F:14])[O:8][CH:7](O)[CH2:6]2.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:17])([C:13]([F:16])([F:14])[F:15])[O:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 184010286-Methoxy-1-methyl-1-(trifluoromethyl)-3,4-dihydro-1H-2-benzopyran-3-ol

Product 1

HCID 102205196-Methoxy-1-methyl-1-trifluoromethylisochromanYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxy-1-methyl-1-trifluoromethyl-isochroman-3-ol (8.36 g, 31.9 mmol) in dichloromethane (84 mL) was added triethylsilane (15.3 mL, 95.8 mmol) followed by trifluoroacetic acid (14.7 mL, 191 mmol). The reaction was stirred at room temperature for 2 hours and was poured into 1N aqueous sodium hydroxide (250 mL). The organic layer was separated and washed with 1N aqueous sodium hydroxide (100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to afford 6-methoxy-1-methyl-1-trifluoromethyl-isochromanas an oil (6.88 g, 88%). 1H NMR (300 MHz, CDCl3) δ1.69 (s, 3), 2.85-2.90 (m, 2), 3.85 (s, 3), 3.90-3.98 (m, 1), 4.14-4.21 (m, 1), 6.72 (d, 1, J=2.6), 6.85 (dd, 1, J=8.7, 2.6), 7.31 (d, 1, J=8.7). 13C NMR (100 MHz, CDCl3) δ23.25, 29.42, 55.19, 61.37, 76.10 (q, J=27.4), 112.84, 113.43, 124.85, 125.96 (q, J=289), 127.86, 136.49, 158.98. IR2946, 2839, 1738, 1611, 1505, 1162, 1137, 1101 cm−1. Analysis calculated for C12H13F3O2: C, 58.54; H, 5.32. Found: C, 58.27; H, 5.35.

Workup

  1. customThe organic layer was separated
  2. washwashed with 1N aqueous sodium hydroxide (100 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f65d2cb8a181488f9b661af8acd107ec
Source dataset
uspto-grants-2002_11
Patent number
US06486325B1

Reaction notes

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