Potassium Carbonate → 1-Tert-butyl 7-ethyl 2-[(methylthio)acetyl]heptanedioate

HRID 2250567Notes

Reaction equation

HRID 2250567 reaction equation
[CH3:1][S:2][CH2:3][C:4](=[O:13])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O>[CH3:1][S:2][CH2:3][C:4]([CH:5]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:6]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4169827Ethyl 5-iodopentanoateHCID 57444537Tert-butyl 4-(methylthio)-3-oxobutanoate

Product 1

HCID 574813391-Tert-butyl 7-ethyl 2-[(methylthio)acetyl]heptanedioateYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(methylthio)-3-oxobutanoate (5.00 g) and potassium carbonate (3.72 g) in dimethylformamide (25 mL) was added ethyl 5-iodopentanoate (6.89 g) and the mixture was stirred at ambient temperature for 15 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (20:1-10:1) to give 1-tert-butyl 7-ethyl 2-[(methylthio)acetyl]heptanedioate as colorless oil (5.88 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of hexane and ethyl acetate (20:1-10:1)

Sources & evidence

ORD record
ord-31f90dc5e5924f60985953b70002fdd8
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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