Chloromethyl Methyl Ether → HCID 57663166、化合物

HRID 548728ノート

反応式

HRID 548728 の反応式
[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

参加物

5

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 57663162HCID 57663162、化合物

生成物 1

HCID 57663166HCID 57663166、化合物収率 53.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0f0dced639174fe5ab4cc7f7db99aa80
出典データセット
uspto-grants-2011_05
特許番号
US07943607B2

反応ノート

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