Sodium Sulfate → HCID 21255871, compound

HRID 365771Notes

Reaction equation

HRID 365771 reaction equation
[Si:1]([O:18][CH2:19][CH:20](OC(=S)C)[C:21]([O:23]C)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.[S:49]([O-])([O-])(=O)=O.[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl.CC(C)=O>[Si:1]([O:18][CH2:19][CH:20]([SH:49])[CH2:21][OH:23])([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 131720782HCID 131720782, compound

Product 1

HCID 21255871HCID 21255871, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-t-butyldiphenylsilyloxy-2-thioacetoxypropionate (example 40) (14.3 g, 34.4 mmol) in dichloromethane (1.0 L) was added diisobutylaluminium hydride (96 mL of 1.5 M solution in toluene, 144 mmol, 4.2 eq) at -78° C. The solution was strirred at -78° C. for 1 hr and at -50° C. for another 1.5 hr. Sodium sulfate decahydrate (15 g) was added and the mixture was warmed at room temperature for 2 hr. Acetone was added and the solution was stirred overnight. Anhydrous sodium sulfate was added and the solution was strirred for 30 min and filtered over a celite diatomaceous earth. The solid was washed several times with acetone and the solvents were evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (85:15) to give the desired compound (4.25 g) in 36% yield.

Workup

  1. waitthe solution was strirred for 30 min
  2. filtrationfiltered over a celite diatomaceous earth
  3. washThe solid was washed several times with acetone
  4. customthe solvents were evaporated under reduced pressure
  5. customThe crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (85:15)

Sources & evidence

ORD record
ord-1514716457d743cb9cf8a925a491134a
Source dataset
uspto-grants-2000_10
Patent number
US06127540

Reaction notes

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