Sodium Sulfate → HCID 21255871, compound

HRID 636867Notes

Reaction equation

HRID 636867 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

Conditions

Temperature
-50 °C

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 stirred 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 stirred for 30 min and filtered over CELITE diatomeceous 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. temperaturethe mixture was warmed at room temperature for 2 hr
  2. stirringthe solution was stirred overnight
  3. stirringthe solution was stirred for 30 min
  4. filtrationfiltered over CELITE diatomeceous earth
  5. washThe solid was washed several times with acetone
  6. customthe solvents were evaporated under reduced pressure
  7. customThe crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (85:15)

Sources & evidence

ORD record
ord-6d1b22c4ded745088479bd248517311c
Source dataset
uspto-grants-2001_02
Patent number
US06194576B1

Reaction notes

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