Diethyl Ether → HCID 53807856, compound

HRID 250537Notes

Reaction equation

HRID 250537 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)O[C:12](=O)[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)=O.[CH3:23]COCC.[OH-:28].[Na+]>C(Cl)Cl>[CH3:23][CH:9]([CH2:10][CH2:11][CH3:12])[C:8](=[O:28])[CH:7]=[CH2:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 159087Triacetoxyperiodinane

Product 1

HCID 53807856HCID 53807856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 13.1 (700 mg, 5.5 mmol) in DCM (10 ml) was added Dess-Martin periodinane reagent (2.57 g, 6.6 mmol) and the solution was stirred at room temperature for 20 minutes. Ether (20 mL) was added to the mixture, and later 15 ml of 1.3 M NaOH solution was added. The mixture was stirred for an additional 10 minutes. After all the precipitate was dissolved into aqueous layer, the solution was extracted with ether (3×50 mL). The combined organic layer was washed with 1.3 M NaOH solution, brine, dried, and concentrated to afford the title compound (500 mg) as colorless oil used in the next step without purification.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for an additional 10 minutes
  3. dissolutionAfter all the precipitate was dissolved into aqueous layer
  4. extractionthe solution was extracted with ether (3×50 mL)
  5. washThe combined organic layer was washed with 1.3 M NaOH solution, brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5c90b4d7a9534e59b61617ddc6ba5a13
Source dataset
uspto-grants-2011_01
Patent number
US07863312B2

Reaction notes

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