Sodium Thiosulfate → 3-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propionaldehyde

HRID 348736Notes

Reaction equation

HRID 348736 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][CH2:21][CH2:22][OH:23])[CH:14]=[CH:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][CH2:21][CH:22]=[O:23])[CH:14]=[CH:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 230791693-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propan-1-ol

Product 1

HCID 230791943-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propionaldehydeYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (1.18 g) obtained in Example 121-6 was dissolved in anhydrous dichloromethane (25 ml) and added with Dess-Martin periodinane (1.82 g), followed by stirring at room temperature for 2 hours. After completion of the reaction, a sodium thiosulfate aqueous solution and a saturated aqueous sodium bicarbonate solution were added to the solution, and the whole was stirred. Then, the solution was extracted with chloroform and the extract was then washed with an aqueous mixture solution of a sodium thiosulfate aqueous solution and a saturated sodium bicarbonate aqueous solution. Then, the organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (981 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. stirringthe whole was stirred
  3. extractionThen, the solution was extracted with chloroform
  4. washthe extract was then washed with an aqueous mixture solution of a sodium thiosulfate aqueous solution
  5. dry with materialThen, the organic layer was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-70af4eed4917440d9197a820f48ee9cb
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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