Chloromethyl Methyl Ether → HCID 57663166, 화합물

HRID 548728노트

반응식

HRID 548728 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 57663166HCID 57663166, 화합물수율 53.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0f0dced639174fe5ab4cc7f7db99aa80
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943607B2

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