Sodium Thiosulfate → HCID 66818288, compound

HRID 1755068Notes

Reaction equation

HRID 1755068 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]([CH:33]1[CH2:38][CH2:37][CH:36]([CH:39]([OH:41])[CH3:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH2:23]([O:30][C:31]([CH:33]1[CH2:38][CH2:37][CH:36]([C:39](=[O:41])[CH3:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 66818020HCID 66818020, compound

Product 1

HCID 66818288HCID 66818288, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (151 mg, 0.355 mmol) was added to a solution of 4-(1-hydroxy-ethyl)-cyclohexanecarboxylic acid benzyl ester (71.6 mg, 0.273 mmol) in anhydrous dichloromethane (0.91 ml) at 0° C. The mixture was stirred at the same temperature for 10 minutes, and further warmed to room temperature and stirred for 4.5 hours. An aqueous sodium thiosulfate solution was added to the reaction solution, followed by extraction with dichloromethane. The organic phase was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 4-acetyl-cyclohexanecarboxylic acid benzyl ester (60.2 mg, 85%).

Workup

  1. stirringstirred for 4.5 hours
  2. extractionfollowed by extraction with dichloromethane
  3. concentrationThe organic phase was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d5b95859547f439d80e96e4a7ce14e56
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…