Methyl iodide → HCID 67996110, compound

HRID 1615138Notes

Reaction equation

HRID 1615138 reaction equation
[CH2:1]([C:4]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][C:7]2([O:12][CH2:11][C:10]([CH3:14])([CH3:13])[CH2:9][O:8]2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].CI.[C:23]([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH3:23][O:19][C:18](=[O:20])[CH2:17][C:4]1([CH2:1][CH:2]=[CH2:3])[CH2:16][CH2:15][C:7]2([O:8][CH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][O:12]2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 67995749HCID 67995749, compound

Product 1

HCID 67996110HCID 67996110, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (9-allyl-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-acetic acid (0.50 g), methyl iodide (0.12 mL), K2CO3 (0.37 g), and N,N-dimethylformamide (5 mL) is stirred at room temperature overnight. 10% aqueous K2CO3 solution is then added and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (MgSO4), and concentrated to give the crude title compound that is used without further purification. Yield: 0.36 g (crude); LC (method 6): tR=1.65 min; Mass spectrum (ESI+): m/z=297 [M+H]+.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. extractionThe combined extract
  3. washis washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-98c617728cb942ae8e9c945d9cff9cf5
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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