反応 #352495

反応方程式

tetrabutylammonium fluoride

3-[(tert-butyldimethylsilyloxy)methyl]-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin

→

title compound

収率 58.0%

3-(Hydroxymethyl)-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin

収率 58.0%

溶媒

THF

acetic acid

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他the reaction
3. 3
   濃縮concentrated in vacuo
4. 4
   その他The residue was partitioned between 20 mL of water and 20 mL ethyl acetate
5. 5
   洗浄The organic phase was washed with 3% solution of aqueous sodium bicarbonate (50 mL), water
6. 6
   乾燥dried over sodium sulfate
7. 7
   濃縮concentrated to a small volume
8. 8
   その他The residue was purified by silica gel chromatography (ethyl acetate-hexane, 1:3)

実験手順

To a stirred solution of the 3-[(tert-butyldimethylsilyloxy)methyl]-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin obtained above (70 mg, 0.16 mmol) in 2 mL THF was added a mixture of 1.0 mL of 1M tetrabutylammonium fluoride in THF and 0.6 mL of acetic acid. The reation mixture was stirred for 7 h until TLC analysis showed the reaction to be complete, then concentrated in vacuo. The residue was partitioned between 20 mL of water and 20 mL ethyl acetate. The organic phase was washed with 3% solution of aqueous sodium bicarbonate (50 mL), water, dried over sodium sulfate, and then concentrated to a small volume. The residue was purified by silica gel chromatography (ethyl acetate-hexane, 1:3) to yield 30 mg (58%) of the title compound; 1H NMR (CDCl3):δ7.60 (dd, J=8.0, J=l.6, 1 H), 7.50 (t, J=8.4, 1 H), 7.08 (t, J=8.0, 1 H), 6.99 (d, J=8.0 Hz, 1 H), 6.54 (d, J=6.0 Hz, 1 H), 6.44 (d, 1 H, J=6.0), 4.76 (s, 2 H), 4.30 (s, 2 H), 1.93 (bs, 1 H); 13C NMR (CDCl3):161.14, 135.73, 133.26, 128.84, 127.31 (q, J=5.4), 126.59, 125.06, 123.33, 120.90, 113.11, 69.45, 64.59; EI-MS:m/z 320.62.

出典