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Acetone → (3RS,4RS)-4-(4-t-butyldimethylsilyloxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman

HRID 1859341
ノート
印刷プレビュー

反応式

HRID 1859341 の反応式
ClCCl.[Si:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2(O)[C:27]3[C:22](=[CH:23][C:24]([O:28][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=3)[S:21][CH2:20][C:19]2([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=2)[CH3:32])=[CH:14][CH:13]=1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].C([BH3-])#N.[Na+].CC(C)=O>[I-].[Zn+2].[I-].O>[Si:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=3)[S:21][CH2:20][C:19]2([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=2)[CH3:32])=[CH:16][CH:17]=1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:5])[CH3:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 221236264-(4-t-Butyldimethylsilyloxyphenyl)-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman

生成物 1

HCID 17871376(3RS,4RS)-4-(4-t-butyldimethylsilyloxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman収率 71%

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 962Water溶媒

実験手順

To dichloromethane solution (30 ml) of 4-(4-t-butyldimethylsilyloxyphenyl)-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman (1.134 g, 1.95 mmol) were added zinc iodide (1.367 g, 4.9 mmol) and sodium cyanoborohydride (797 mg, 12.7 mmol), and the resulting mixture was stirred for 2 hours at room temperature. After adding acetone (5 ml) and water, the reaction solution was extracted with dichloromethane and the organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the organic solvent. The crude product thus obtained was purified with silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 783 mg (yield: 71%) of the title compound.

後処理

  1. extractionthe reaction solution was extracted with dichloromethane
  2. washthe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the organic solvent
  6. customThe crude product thus obtained
  7. customwas purified with silica gel column chromatography (ethyl acetate:hexane=1:4)

出典と根拠

ORDレコード
ord-b0764377608c44b9b59b8becd520455c
出典データセット
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06153768

反応ノート

読み込み中…

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