反応 #352493

反応方程式

tetrabutylammonium fluoride

3-[(tert-butyldimethylsilyloxy)methyl]-6-[[3-(N,N-dimethylamino)-phenyloxy]methyl]-1,2-dithiin

→

title compound

収率 84.0%

3-(Hydroxymethyl)-6-[[3-(N,N-dimethylamino)phenyloxy]methyl]-1,2-dithiin

収率 84.0%

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 40 mL of water and 60 mL ethyl acetate
5. 5
   洗浄The organic phase was washed with dilute aqueous sodium bicarbonate, water
6. 6
   乾燥dried over sodium sulfate
7. 7
   その他evaporated to a small volume
8. 8
   その他The residue was chromatographed over silica gel column (ethyl acetate-hexane, 1:1)

実験手順

To a stirred solution of the 3-[(tert-butyldimethylsilyloxy)methyl]-6-[[3-(N,N-dimethylamino)-phenyloxy]methyl]-1,2-dithiin obtained above (100 mg, 0.24 mmol) in 2 mL THF was added a mixture of 2.4 mL of 1M tetrabutylammonium fluoride in THF and 1.4 mL of acetic acid. The reation mixture was stirred for 3 h until TLC analysis showed the reaction to be complete, then concentrated in vacuo. The residue was partitioned between 40 mL of water and 60 mL ethyl acetate. The organic phase was washed with dilute aqueous sodium bicarbonate, water, dried over sodium sulfate, and then evaporated to a small volume. The residue was chromatographed over silica gel column (ethyl acetate-hexane, 1:1) to yield 60.5 mg (84.0%) of the title compound. Further purification was accomplished by reverse-phase HPLC (PRP-1 column, acetonitrile-water, 2:3); 1H-NMR (CDCl3) δ7.3 (bs, 1 H), 7.1 (bs, 1 H), 6.64 (s, 1 H), 6.55 (d, J=7.2, 1 H), 6.46(d, J=5.6, 1 H), 6.41 (d, J=5.6, 1 H), 4.65 (s, 2 H), 4.30 (s, 2 H), 2.69 (s, 6 H).

出典