Chloromethyl Methyl Ether → HCID 66800403, compound

HRID 1057159Notes

Reaction equation

HRID 1057159 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:14][C:13](=[O:15])[O:12][N:11]=2)=[CH:6][CH:5]=1.Cl[CH2:17][O:18][CH3:19]>C1COCC1>[I:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:14]=[C:13]([O:15][CH2:17][O:18][CH3:19])[O:12][N:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 66800424HCID 66800424, compound

Product 1

HCID 66800403HCID 66800403, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (360 mg, 9.0 mmol, 60% in mineral oil) was added into a solution of 3-(4-iodophenyl)isoxazol-5(4H)-one (2.0 g, 6.97 mmol) in anhydrous THF (20 mL) at 0° C. The mixture was stirred at 0° C. for 2 h. Chloro(methoxy)methane (1.12 g, 14 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 2 h, poured into ice-water, and extracted with EtOAc (3×60 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified on a silica gel column using EtOAc in petroleum ether (1:20) to afford the title compound as pale solid (960 mg, 42%). 1H NMR (DMSO-d6, 400 MHz): δ 7.96 (d, 2H), 7.45 (d, 2H), 5.99 (s, 1H), 4.95 (s, 2H), 3.27 (s, 3H). LCMS: 332 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 h
  2. extractionextracted with EtOAc (3×60 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-f277fdef67424133901e21ed16c1631c
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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