Sodium Hydroxide → HCID 86650674, compound

HRID 601754Notes

Reaction equation

HRID 601754 reaction equation
[CH3:1][C:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[C:3]=1[CH2:9][CH2:10][OH:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>ClCCl>[CH3:1][C:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[C:3]=1[CH2:9][CH:10]=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 66757195HCID 66757195, compound

Product 1

HCID 86650674HCID 86650674, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(3-Methyl-bicyclo[2.2.1]hept-2-en-2-yl)-ethanol (16.37 g, 107.53 mmol) was dissolved in dichloromethane (150 ml) and Dess-Martin periodinane in solution in dichloromethane (15%, 536.2 g, 189.7 mmol) was added at room temperature over a 110 minutes period under nitrogen. The mixture was further stirred at room temperature for 30 minutes and was hydrolyzed with aqueous NaOH 5% in an ice-bath, and extracted 3 times with Et2O. The combined organic layers were washed with H2O, brine, dried over Na2SO4, and filtered off. Solvents were removed under reduced pressure to give a crude which was further purified by bulb to bulb distillation under reduced pressure to afford the desired compound (13.468 g, 88% purity) in 83% yield.

Workup

  1. extractionextracted 3 times with Et2O
  2. washThe combined organic layers were washed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered off
  5. customSolvents were removed under reduced pressure
  6. customto give a crude which
  7. distillationwas further purified by bulb to bulb distillation under reduced pressure

Sources & evidence

ORD record
ord-cee370c49521403aa113cbb03a76650b
Source dataset
uspto-grants-2011_03
Patent number
US07902393B2

Reaction notes

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