Chloromethyl Methyl Ether → HCID 86652365, compound

HRID 2272817Notes

Reaction equation

HRID 2272817 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8](=[O:13])[O:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:34][O:35][CH2:36]Cl>CN(C)C=O>[CH3:34][O:35][CH2:36][O:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:8](=[O:13])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 10782279HCID 10782279, compound

Product 1

HCID 86652365HCID 86652365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl 7-hydroxy-8-methyl-2-oxo-2H-chromen-3-ylcarbamate 7 (975 mg, 3.0 mmol) in anhydrous N,N-dimethylformamide (15 mL) was added N,N-diisopropylethylamine (1.01 mL, 7.5 mmol) over 5 minutes at room temperature. The resulting solution was stirred for 30 minutes and cooled to 0° C. To it was added methoxymethylchloride (1.25 mL, 7.5 mmol) dropwise and the resulting mixture was stirred at room temperature for 3 hours. The reaction was quenched by water and the precipitate was filtered, washed with diethyl ether and dried under vacuum to give compound 8 as a white amorphous solid (931 mg, 82%). 1H NMR (500 MHz, acetone-d6) δ 8.26 (s, 1H), 8.10 (s, 1H), 7.42 (m, 6H), 7.15 (d, 1H, J=8.7 Hz), 5.34 (s, 2H), 5.26 (s, 2H), 3.49 (s, 3H), 2.29 (s, 3H). 13C NMR (100 MHz, acetone-d6) δ 158.8, 157.2, 154.2, 149.9, 137.4, 129.3, 129.0, 128.9, 126.2, 123.1, 112.8, 115.0, 114.9, 112.3, 95.6, 67.6, 56.4, 8.3. IR (KBr) νmax 3321, 2948, 2931, 28591, 1724, 1693, 1608, 1541, 1367, 1213, 1155, 898 cm−1. HRMS (ESI+) m/z [M+Na+] calcd for C20H19NNaO6 392.1110. found 392.1104.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. customThe reaction was quenched by water
  3. filtrationthe precipitate was filtered
  4. washwashed with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ac8e3269a93744509b54e156444f88ce
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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