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

HRID 1859341Notes

Reaction equation

HRID 1859341 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b0764377608c44b9b59b8becd520455c
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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