Sodium Thiosulfate → 9-Hydroxy-5,9-dimethyl-decanal

HRID 493069Notes

Reaction equation

HRID 493069 reaction equation
[CH3:1][C@@H:2]([CH2:8][CH2:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])[CH2:3][CH2:4][CH2:5][CH2:6][OH:7].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+]>C(Cl)Cl>[OH:13][C:11]([CH3:12])([CH3:14])[CH2:10][CH2:9][CH2:8][CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]=[O:7]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 15859989(R)-5,9-dimethyl-decane-1,9-diol

Product 1

HCID 218389029-Hydroxy-5,9-dimethyl-decanalYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of diol 14 (25 mg, 0.12 mmol) in anhydrous CH2Cl2 (3.5 mL) was added Dess-Martin reagent (73 mg, 0.15 mmol) at room temperature. The reaction was stirred at room temperature for 1.5 hours. Then, an aqueous solution of sodium thiosulfate (6 mL) and saturated NaHCO3 (6 mL) were added. The reaction was extracted with CH2Cl2, solvents were removed under reduced pressure, and the crude oil was purified on silica Sep-Pak using hexane/EtOAc (7:3) as an eluent to give an oily aldehyde 15 (16.5 mg, 67%).

Workup

  1. extractionThe reaction was extracted with CH2Cl2, solvents
  2. customwere removed under reduced pressure
  3. customthe crude oil was purified on silica Sep-Pak

Sources & evidence

ORD record
ord-04b62b99c1f547bda46c3ce7d97e2253
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

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