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

HRID 1859341
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HRID 1859341 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b0764377608c44b9b59b8becd520455c
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06153768

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