Methyl iodide → {2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 474725노트

반응식

HRID 474725 반응식
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29]I>C1COCC1.[H-].[Na+]>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([C:24]([F:25])([F:26])[F:27])[CH:18]=2)=[CH:14][CH:15]=1)[CH3:29])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 6328Methyl iodideHCID 67774886{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

생성물 1

HCID 67775169{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester수율 95.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 24758Sodium hydride용매

실험 절차

{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (1.1 g, 2.64 mmol, 1 eq) was dissolved in dry THF (18 ml) and NaH, 60% (316 mg, 7.92 mmol, 3 eq) was added. After 30 min, the reaction mixture was treated with methyl iodide (1.65 ml, 2.64 mmol, 10 eq) and was stirred for 3.5 h. The excess NaH was quenched by a slow addition of water, diluted with brine (40 ml) and extracted with Et2O (3×40 ml). Combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated to give a product without further purification {2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester (1.08 g, yield=56.1%, purity=59%). [M+H]+=430.87 1H NMR (300 MHz; CDCl3) δ/ppm 1.38-1.48 (s, 9H), 2.74-2.90 (m, 4H), 3.38-3.50 (m, 2H), 6.93-7.08 (m, 3H), 7.15-7.31 (m, 3H), 7.41 (t, J=8.43 Hz, 1H)

후처리

  1. customThe excess NaH was quenched by a slow addition of water
  2. additiondiluted with brine (40 ml)
  3. extractionextracted with Et2O (3×40 ml)
  4. dry with materialCombined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a product

출처 및 근거

ORD 기록
ord-d2befc945bcb4b34b386668b038f5d37
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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