Triethylamine → (2-Methoxy-6-methylbenzyl)phthalimide

HRID 1582244

反応式

HRID 1582244 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1[CH2:5]O.C(N(CC)CC)C.CS(Cl)(=O)=O.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.[K]>C(Cl)Cl.CN(C=O)C.CCOC(C)=O.[Cl-].[Na+].O.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1[CH2:5][C:33]1[CH:32]=[CH:31][CH:30]=[C:26]2[C:27]([NH:28][C:24](=[O:34])[C:25]=12)=[O:29]

参加物

10

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13208697(2-Methoxy-6-methylphenyl)methanolHCID 24194345Phthalimide potassium salt

生成物 1

HCID 21985073(2-Methoxy-6-methylbenzyl)phthalimide収率 66.4%

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 2-methoxy-6-methylbenzyl alcohol (0.96 g, 6.32 mmol) in CH2Cl2 (35 mL) was added triethylamine (2.00 mL, 14.35 mmol) followed by methanesulfonyl chloride (0.90 mL, 11.63 mmol) and the resultant solution was heated at 40° C. for 45 minutes then cooled to room temperature. The mixture was diluted with CH2Cl2 (35 mL), washed with brine (3×15 mL), dried (Na2SO4), and concentrated to provide a pale yellow solid. The solid (1.12 g) was dissolved in DMF (35 mL), treated with potassium phthalimide (2.62 g, 14.15 mmol), and heated at 80° C. overnight. The mixture was cooled to room temperature and diluted with EtOAc (70 mL), brine (35 mL), and water (20 mL). The phases were separated and the organic phase was washed with 1.0 N NaOH (6×10 mL) and brine (2×20 mL). The organic phase was dried (MgSO4) and concentrated to provide an pale yellow solid. The solid was rinsed with hexanes (3×10 mL) and provided 1.18 g (66%) of (2-methoxy-6-methylbenzyl)phthalimide as a white solid. 1H NMR (CDCl3) δ2.53 (s, 3H), 3.75 (s, 3H), 4.89 (s, 2H), 6.70 (d, 1H, J=8.4 Hz), 6.80 (d, 1H), J=7.5 Hz), 7.15 (dd, 1H, J=7.5, 8.4 Hz), 7.66-7.68 (m, 2H), 7.76-7.80 (m, 2H); —C NMR (CDCl3) δ20.27, 34.95, 55.90, 108.61, 122.38, 123.17, 123.41, 128.97, 132.60, 134.07, 139.55, 158.70, 168.36.

後処理

  1. washwashed with brine (3×15 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto provide a pale yellow solid
  5. temperatureheated at 80° C. overnight
  6. temperatureThe mixture was cooled to room temperature
  7. customThe phases were separated
  8. washthe organic phase was washed with 1.0 N NaOH (6×10 mL) and brine (2×20 mL)
  9. dry with materialThe organic phase was dried (MgSO4)
  10. concentrationconcentrated
  11. customto provide an pale yellow solid
  12. washThe solid was rinsed with hexanes (3×10 mL)

出典と根拠

ORDレコード
ord-efbdeaad910a460a9a7b698659a502c9
出典データセット
uspto-grants-2004_05
特許番号
US06734191B2

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