Sodium Sulfate → HCID 21255871, compound

HRID 618836Notes

Reaction equation

HRID 618836 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 celite. 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 celite
  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-f00dc71313024aed9e9ecf7a3cf2a961
Source dataset
uspto-grants-1999_09
Patent number
US05955610

Reaction notes

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