Sodium Chloride → HCID 68541861, compound

HRID 1446694Notes

Reaction equation

HRID 1446694 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[Na+].[I:7][C:8]1[CH:9]=C(C(=O)CC)C=C[CH:13]=1.CI.[Cl-].[Na+].[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>C(OCC)(=O)C.O.CN1C(=O)CCC1>[I:7][C:8]1[CH:13]=[C:22]([C:26](=[O:25])[C:2]([CH3:4])([CH3:3])[CH3:1])[CH:23]=[CH:24][CH:9]=1

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 11196234HCID 11196234, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 68541861HCID 68541861, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

Combine NaOtBu (3.6 g, 4 equiv.), THF (10 mL), and NMP (10 mL) in a round bottomed flask. Place under nitrogen and cool to 0° C. Dissolve 1-(3-iodo-phenyl)-propan-1-one (2 g, 9.4 mmol) in THF (10 mL) and add dropwise to the reaction. Immediately following, add methyl iodide (2.3 mL, 4 equiv.) via syringe. Stir at 0° C. for 5 hours. Quench reaction with water then dilute with ethyl acetate. Wash organics with water then aqueous saturated sodium chloride. Dry over magnesium sulfate, filter and concentrate in vacuo. Purify by silica chromatography (Hex→5% EtOAc:Hexanes) to give 2.0 g clear liquid. 1H NMR (400 MHz, DMSO-d6) δ 7.70 (m, 2H), 7.66 (m, 1H), 7.40 (m, 1H), 1.23 (s, 9H).

Workup

  1. customQuench
  2. customreaction with water
  3. dry with materialDry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by silica chromatography (Hex→5% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-26b9734c55b946498f148510e24c2cbd
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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