Iodoethane → 2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-ethyl-butyric acid methyl ester

HRID 658911Notes

Reaction equation

HRID 658911 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13](=[O:30])[CH:14]([O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[CH:25]1[O:29][CH2:28][CH2:27][O:26]1)[CH2:15][CH3:16].I[CH2:32][CH3:33]>C1COCC1.C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:30])[C:14]([O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[CH:25]1[O:29][CH2:28][CH2:27][O:26]1)([CH2:32][CH3:33])[CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 2733832Lithium HexamethyldisilazideHCID 594280712-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-butyric acid methyl ester

Product 1

HCID 594280672-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-ethyl-butyric acid methyl esterYield 97.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium bis(trimethylsilyl)amide (60 mL, 60 mmol, 1 M in THF) was slowly added to a solution of 2-(4-chloro-2-[1,3]dioxolan-2-yl-phenoxy)-butyric acid methyl ester (15 g, 50 mmol) in anhydrous THF (150 mL) at −78° C. After the mixture was stirred for 15 min, iodoethane (9.3 g, 60 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 crude product as a oil (16 g).

Workup

  1. stirringstirred for 2 h
  2. washwashed with a saturated aqueous solution of NH4Cl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c66e26e1419f400894ccecd38616d89d
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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