Iodine → HCID 69596313, compound

HRID 2212576Notes

Reaction equation

HRID 2212576 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18]Cl)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].II>C1COCC1.C(OCC)(=O)C.[Zn]>[CH3:26][O:25][C:23](=[O:24])[CH2:22][C:15]1([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17][CH2:18][O:20]1

Participants

7

Reactant 3

HCID 807IodineHCID 60984Methyl bromoacetateHCID 21966699HCID 21966699, compound

Product 1

HCID 69596313HCID 69596313, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Benzyloxy-phenyl)-4-chloro-butan-1-one (0.3 g, 1.04 mmol) was combined with methyl bromoacetate (0.24 g, 1.56 mmol) and zinc metal (0.05 g, 2.08 mmol) in THF (15 mL), a catalytic amount of iodine was added, and the reaction was heated to reflux for 18 h. The reaction was taken up in ethyl acetate, washed with water and brine, dried over magnesium sulfate, and concentrated to give [2-(4-benzyloxy-phenyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester (0.3 g, 92%) as an oil. MS found: (M+H)+=327.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 18 h
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9819c1fd214b4ab08d14341a4055f6e8
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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