3-(Dimethylamino)phenol → 6-[[3-(N,N-dimethylamino)-phenyloxy]methyl]-1,2-dithiin

HRID 265310

反応式

OC[C:3]1[S:4][S:5][C:6]([CH2:9][O:10][Si](C(C)(C)C)(C)C)=[CH:7][CH:8]=1.[CH3:18][N:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23](O)[CH:22]=1)[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:18][N:19]([C:21]1[CH:22]=[C:23]([O:10][CH2:9][C:6]2[S:5][S:4][CH:3]=[CH:8][CH:7]=2)[CH:24]=[CH:25][CH:26]=1)[CH3:20]

参加物

反応条件

温度: 0 °C

実験手順

To a stirred solution of 200 mg (0.688 mmol) of 3-(hydroxymethyl)-6-[(tert-butyldimethylsilyloxy)methyl]-1,2-dithiin (U.S. Ser. No. 08/212,096) in 2 mL dry THF was added a solution of 3--N,N-dimethylaminophenol (190 mg, 1.376 mmol) in 2 mL THF, followed by addition of (220 mg, 0.839 mmol) triphenylphosphine. The resulting solution was cooled to 0° C., then 140 μL (155 mg, 0.890 mmol) of diethylazodicarboxylate was added, and the reaction mixture was kept at 0°-5° C. for 3 h until TLC analysis showed the reaction to be complete. For isolation of the products the reaction mixture was chromatographed directly on silica gel column, using ethyl acetate-hexane, 1:3 to yield 3-[tert-butyldimethylsilyloxy)methyl]-6-[[3-(N,N-dimethylamino)-phenyloxy]methyl]-1,2-dithiin (115 mg, 41.1%); 1H-NMR (CDCl3) δ7.3 (bs, 1 H), 7.1 (bs, 1 H), 6.60 (d, J=2.4, 1 H), 6.52 (bd, J=7.27 1 H), 6.42 (d, J=6.0, 1 H), 6.34 (d, J=6.0, 1 H), 4.60 (s, 2 H), 4.26 (s, 2 H), 2.65 (s, 6 H), 0.88 (s, 9 H), 0.07 (s, 6 H).

後処理

customthe reaction
customFor isolation of the products the reaction mixture was chromatographed directly on silica gel column

出典と根拠

ORDレコード: ord-0abb10cc76074099818aab159509c646
出典データセット: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05648354

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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