Chloromethyl Methyl Ether → HCID 57663166, compound

HRID 548728Notes

Reaction equation

HRID 548728 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:16]=[CH:15][C:7]2[C:8](=[O:14])[NH:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=1.Cl[CH2:18][O:19][CH3:20]>C1COCC1>[F:3][C:4]1[CH:16]=[CH:15][C:7]2[C:8](=[O:14])[N:9]([CH2:18][O:19][CH3:20])[C:10]([CH3:12])([CH3:13])[O:11][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 57663162HCID 57663162, compound

Product 1

HCID 57663166HCID 57663166, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil) (45 mg, 1.13 mmol) was added to a solution of 7-fluoro-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one (0.2 g, 1.02 mmol) in THF (4 mL) at 0° C., under argon then allowed to warm to RT and chloromethylmethyl ether (0.086 mL, 1.13 mmol) added. The reaction was stirred at RT for 4 hours then poured into ice/water (50 mL) and extracted into ethyl acetate (50 mL). The organics were washed with brine (50 mL), dried (MgSO4), and the solvent removed in vacuo. The crude oil was chromatographed on silica, eluting with 10-50% ethyl acetate in isohexane, to give the desired compound as a white solid (0.13 g). 1H NMR δ (CDCl3): 1.66 (s, 6H), 3.31 (s, 3H), 5.00 (s, 2H), 6.53 (d, 1H), 6.67-6.72 (m, 1H), 7.89 (dd, 1H).

Workup

  1. extractionextracted into ethyl acetate (50 mL)
  2. washThe organics were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe crude oil was chromatographed on silica
  6. washeluting with 10-50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-0f0dced639174fe5ab4cc7f7db99aa80
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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