Hydrochloric Acid → HCID 23023492, compound

HRID 2222449Notes

Reaction equation

HRID 2222449 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[O:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[C:18]([O:20][CH3:21])=[O:19].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1.Cl>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][C:14]1([C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:16][CH2:17][O:13]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 169922Methyl tetrahydrofuran-2-carboxylateHCID 40672073-Methoxybenzyl bromideHCID 178418339Butyllithium

Product 1

HCID 23023492HCID 23023492, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.44 g of diisopropylamine in 20 ml of tetrahydrofuran were sequentially added 26 ml of 1.6 M solution of n-butyllithium in hexane, 5.30 g of methyl tetrahydro-2-furancarboxylate in 20 ml of tetrahydrofuran and 8.85 g of 1-bromomethyl-3-methoxybenzene in 25 ml of tetrahydrofuran at −70° C. under an atmosphere of nitrogen gas. After warming to room temperature, 100 ml of 1N hydrochloric acid and 200 ml of ethyl acetate were added. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 6.01 g of the title compound from the 4:1 hexane-ethyl acetate fraction.

Workup

  1. customat −70° C.
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3ea028b35f894ef99fe94cacefb314ca
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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