Water → 4-[9-(t-Butyldimethylsilyloxy)1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1792300ノート

反応式

HRID 1792300 の反応式
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]1(O)[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]1([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[CH3:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].O>ClCCCl.[I-].[Zn+2].[I-]>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]1([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[CH3:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 220331564-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

生成物 1

HCID 220334284-[9-(t-Butyldimethylsilyloxy)1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman収率 50.3%

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (5.40 g, 9.49 mmol) in 1,2-dichloroethane (150 ml) were added zinc iodide (4.54 g, 14.23 mmol) and sodium cyanoborohydride (4.47 g, 71.17 mmol), which was then stirred at room temperature for 12 hours. After the reaction was completed, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=9:1) to give the title compound (2.64 g, yield 50%, 3RS/4RS:3RS/4SR=6:1) as a colorless oil.

後処理

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-633ebe28f90a49ec92db8c9daf1faa33
出典データセット
uspto-grants-2006_07
特許番号
US07074819B2

反応ノート

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