Sodium Thiosulfate → HCID 19077120, compound

HRID 964514Notes

Reaction equation

HRID 964514 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][CH:9]3[CH2:18][CH2:19][OH:20])=[CH:4][C:3]1=2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1([CH3:21])[CH2:15][CH2:14][C:13]([CH3:16])([CH3:17])[C:12]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][CH:9]3[CH2:18][CH:19]=[O:20])=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 19077085HCID 19077085, compound

Product 1

HCID 19077120HCID 19077120, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above alcohol (60 mg, 0.21 mmol) was dissolved in dichloromethane (5.0 mL) and Dess-Martin reagent (2×135 mg, 0.63 mmol) was added in two portions and stirred for 60 min. A saturated solution of sodium bicarbonate (3.0 mL) was added, followed by solid sodium thiosulfate. The mixture was stirred vigorously and extracted with dichloromethane. The organic layer was washed with water (2×5 mL), brine (2×5 mL) and dried over MgSO4. The solvent was evaporated and the residue was purified over a short silica gel chromatography column to give 48 mg of the desired aldehyde, (+)-2-(1,2,3,4,5,6,7,8-octahydro-5,5,8,8-tetramethylanthracen-1-yl)ethan-1-al (81% yield).

Workup

  1. stirringThe mixture was stirred vigorously
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water (2×5 mL), brine (2×5 mL)
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated
  6. customthe residue was purified over a short silica gel chromatography column

Sources & evidence

ORD record
ord-04d4795ac1504046a31be32a609fa95e
Source dataset
uspto-grants-1998_06
Patent number
US05770383

Reaction notes

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