Diethyl Ether → (+/-)-cis-4-(Cyanomethyl)-1,5dioxaspiro[5.5]undecane-2-acetic acid

HRID 1886277Notes

Reaction equation

HRID 1886277 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[O:14]=[CH:15][CH2:16][C@H:17]1[O:22][C:21]2([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[O:20][C@@H:19]([CH2:28][C:29]#[N:30])[CH2:18]1.C(OCC)C>CC(C)=O>[C:29]([CH2:28][C@H:19]1[O:20][C:21]2([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[O:22][C@@H:17]([CH2:16][C:15]([OH:3])=[O:14])[CH2:18]1)#[N:30]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 86744692(+/-)-cis-4-(2-Oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrileHCID 131709961Jones' reagent

Product 1

HCID 15045140(+/-)-cis-4-(Cyanomethyl)-1,5dioxaspiro[5.5]undecane-2-acetic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent (chromium trioxide-sulfuric acid-water), 4.4 mL (8.85 mmol), is added dropwise to a 0° C. solution of (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile, 3.62 g (12.6 mmol), dissolved in 30 mL of acetone until the orange color is not discharged. After stirring a further 15 minutes, the mixture is poured into 300 mL of diethyl ether and washed with brine until the aqueous washes are colorless. The diethyl ether layer is dried (magnesium sulfate), filtered, and concentrated to provide 3.65 g of (±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid as a yellow solid.

Workup

  1. washwashed with brine until the aqueous washes
  2. dry with materialThe diethyl ether layer is dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2f67d8811d954f05911e79e240b1f886
Source dataset
uspto-grants-1992_09
Patent number
US05149837

Reaction notes

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