Sodium Thiosulfate → HCID 178501146, compound

HRID 1482886Notes

Reaction equation

HRID 1482886 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH2:26]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[CH:24]([C@H:25]1[CH2:26][CH2:27][C@H:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:29][CH2:30]1)=[O:23]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 178501147HCID 178501147, compound

Product 1

HCID 178501146HCID 178501146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Dess-Martin periodinane (542 mg, 1.28 mmol) in THF (2 mL) was added methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (200 mg, 1.18 mmol) at 0° C., and the reaction mixture was then stirred at 20° C. for 3 hours before the addition of saturated aqueous sodium thiosulfate solution (50 mL). The mixture was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by prep-TLC (ethyl acetate/petroleum ether) to give methyl trans-4-formylcyclohexanecarboxylate. MS ESI calc'd. for C9H15O3[M+H]+ 171. found 171. 1H NMR: (400 MHz, CDCl3) δ 9.63 (s, 1H), 3.68 (s, 3H), 2.36-2.17 (m, 2H), 2.13-2.04 (m, 4H), 1.55-1.45 (m, 2H), 1.37-1.25 (m, 2H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep-TLC (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-ef55d95d3bfb4379bb406ffd8f2ec36c
Source dataset
uspto-grants-2016_08
Patent number
US09416111B2

Reaction notes

Loading…