1-Iodopropane → 2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-propyl pentanoic acid ethyl ester

HRID 658928Notes

Reaction equation

HRID 658928 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]([O:13][C:14](=[O:32])[CH:15]([O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[CH:27]1[O:31][CH2:30][CH2:29][O:28]1)[CH2:16][CH2:17][CH3:18])[CH3:12].I[CH2:34][CH2:35][CH3:36]>C1COCC1.C(OCC)(=O)C>[CH2:11]([O:13][C:14](=[O:32])[C:15]([O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[CH:27]1[O:31][CH2:30][CH2:29][O:28]1)([CH2:34][CH2:35][CH3:36])[CH2:16][CH2:17][CH3:18])[CH3:12]

Participants

6

Reactant 3

HCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 59428066HCID 59428066, compound

Product 1

HCID 594280792-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-propyl pentanoic acid ethyl esterYield 67.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Lithium bis(trimethylsilyl)amide (26 mL, 26 mmol, 1 M in THF) was slowly added to a solution of 2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-pentanoic acid ethyl ester (6.6 g, 20 mmol) in 60 mL of anhydrous THF at −78° C. After the mixture was stirred for 30 min at −78° C., 1-Iodopropane (4 mL, 40 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 2 h. Then the mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of NH4Cl, dried over anhydrous Na2SO4 and concentrated to give the title compound as a yellow oil (5 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 h
  3. washwashed with a saturated aqueous solution of NH4Cl
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-936982ba286b4c32838838679d158317
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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