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

HRID 1582244

반응식

HRID 1582244 반응식
[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]

참가 물질

10

반응물 4

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

생성물 1

HCID 21985073(2-Methoxy-6-methylbenzyl)phthalimide수율 66.4%

시약·촉매·용매 5

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-efbdeaad910a460a9a7b698659a502c9
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734191B2

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