Iodoethane → HCID 67160418, compound

HRID 2388772Notes

Reaction equation

HRID 2388772 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].I[CH2:13][CH3:14]>>[CH2:13]([O:8][CH2:7][C@@H:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1)[CH3:14]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 7528SolketalHCID 24758Sodium hydride

Product 1

HCID 67160418HCID 67160418, compound

Procedure

To a solution of 2,2-dimethyl-1,3-dioxolane-4-methanol (1.5 g), in dimethylfomylamide (30 mL), 60% sodium hydride (0.50 g) was added portion-wise at 0° C. then warmed to ambient temperature. Iodoethane (3.5 mL) was added to the mixture at 0° C. then stirred for 16 h at room temperature. The reaction mixture was filtered then the filtrate was diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O (×2) then brine and dried (MgSO4), filtered and evaporated. Purification was by column chromatography on silica gel using EtOAdEt2O (1:1) as eluent to give the subtitle compound as clear, colourless oil. Yield: 1 g

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was diluted with H2O
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with H2O (×2)
  5. dry with materialbrine and dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification

Sources & evidence

ORD record
ord-c6544a5c4a994102bebe3c3b064deeb0
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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