Chloromethyl Methyl Ether → 5-(4-Iodophenyl)-3-(methoxymethoxy)isoxazole

HRID 1057156Notes

Reaction equation

HRID 1057156 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([OH:13])[CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:15][O:16][CH3:17]>CCN(CC)CC.CS(C)=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([O:13][CH2:15][O:16][CH3:17])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 178515628HCID 178515628, compound

Product 1

HCID 668003885-(4-Iodophenyl)-3-(methoxymethoxy)isoxazoleYield 40%

Reagents, catalysts & solvents 1

HCID 86583882DMSO triethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(4-iodophenyl)isoxazol-3-ol (128 mg, 0.43 mmol) in Et3N/DMSO (10:1 v/v, 5.5 mL) at 0° C., chloro(methoxy)methane (45 mg, 0.64 mmol) was added dropwise. After stirring at 0° C. for 0.5 h, the reaction mixture was poured into ice-water (50 mL) and extracted with EtOAc (3×20 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 white solid (55 mg, 40%). 1H NMR (DMSO-d6, 400 MHz): δ 7.79 (d, 2H), 7.46 (d, 2H), 6.23 (s, 1H), 5.36 (s, 2H), 3.57 (s, 3H). LCMS: 332 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-6f3d944181554ebf8930742908734d39
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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