Hexamethyldisilazane → 1-(3-Cyclopentoxy-4-methoxyphenyl)propylamine

HRID 2349

반응식

HRID 2349 반응식
C[Si](C)(C)N[Si](C)(C)C.C([Li])C[CH2:12][CH3:13].[CH:15]1([O:20][C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH:24]=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.C([Mg]Br)C.[Cl-].[NH4+:36]>O1CCCC1.CC#N.CCCCCC>[CH:15]1([O:20][C:21]2[CH:22]=[C:23]([CH:24]([NH2:36])[CH2:12][CH3:13])[CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

9

반응물 5

HCID 13838HexamethyldisilazaneHCID 25517Ammonium ChlorideHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 178418339ButyllithiumHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 196901641-(3-Cyclopentoxy-4-methoxyphenyl)propylamine

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To an ice bath cooled stirred solution of 1,1,1,3,3,3-hexamethyldisilazane (2.5M, 4.1 mL, 19.5 mmol) in tetrahydrofuran (5 mL) under nitrogen, was added a hexane solution of butyl lithium (7.2 mL, 18 mmol) via syringe. The ice bath was removed and the solution was stirred for 30 minutes at room temperature. This solution then was added dropwise to an ice bath cooled solution of 3-cyclopentoxy-4-methoxybenzaldehyde (3.3 g, 15 mmol) in tetrahydrofuran (5 mL) and the mixture stirred for 20 minutes. An ethereal solution of ethylmagnesium bromide (3M, 10 mL, 30 mmol) then was added dropwise. The reaction solution was allowed to reach room temperature and then was stirred at room temperature. The reaction progress was monitored by HPLC (Waters Nova-Pak/EC 18 column, 3.9×150 mm, 4 micron, 1 mL/min, 240 nm, 35/65, CH3CN/0.1% H3PO4 (aq)) and after 3 hours no starting material remained. The reaction mixture was slowly poured into a saturated solution of ammonium chloride (100 mL). The resulting mixture was extracted with methylene chloride (3×20 mL) and the combined extracts were dried over magnesium sulfate and concentrated in vacuo to yield 5.6 g of product which was further purified by flash column chromatography (silica gel, 250/10/1, methylene chloride/methanol/ammonium hydroxide) to afford 2.5 g (67%) of the product as an oil: 1H NMR (CDCl3) δ 6.91-6.77 (m, 3H), 4.85-4.74 (m, 1H), 3.83 (s, 3H), 3.74 (t, J=6.8 Hz, 1H), 2.02-1.15 (m, 12H), 0.86 (t, J=7.4 Hz, 3H); 13C NMR (CDCl3) δ 148.8, 147.5, 138.8, 118.4, 113.3, 111.8, 80.3, 57.4, 56.0, 32.7, 32.4, 10.9.

후처리

  1. temperatureTo an ice bath cooled
  2. customThe ice bath was removed
  3. additionThis solution then was added dropwise to an ice bath
  4. stirringthe mixture stirred for 20 minutes
  5. customto reach room temperature
  6. stirringwas stirred at room temperature
  7. extractionThe resulting mixture was extracted with methylene chloride (3×20 mL)
  8. dry with materialthe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-48bcadbbba7b4f4299bd816594d61a87
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728844

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