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Water → 4-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1792306
ノート
印刷プレビュー

反応式

HRID 1792306 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][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=2)[O:21][CH2:20][C:19]1([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=1)[CH3:32])([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][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=2)[O:21][CH2:20][C:19]1([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=1)[CH3:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 220330974-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

生成物 1

HCID 220331314-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman収率 50%

試薬・触媒・溶媒 2

HCID 9883512
zinc(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-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (3.10 g, 5.06 mmol) in 1,2-dichloroethane (200 ml) were added zinc iodide (2.42 g, 7.59 mmol) and sodium cyanoborohydride (2.23 g, 35.42 mmol), which was then stirred at room temperature for 8 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 (1.50 g, yield 50%, 3RS/4RS:3RS14SR=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-f9d1a179e0a541f8bfbcd308542cc988
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07074819B2

反応ノート

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