6-Bromohexanenitrile → 6-(3-[4-(5-Cyanopentyloxy)phenyl]propoxy}hexanenitrile

HRID 32788

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HRID 32788 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19]>CN(C=O)C>[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19])=[CH:6][CH:7]=1)#[N:19]

참가 물질

4

반응물 2

HCID 810936-BromohexanenitrileHCID 824523-(4-Hydroxyphenyl)propanol

생성물 1

HCID 219598576-(3-[4-(5-Cyanopentyloxy)phenyl]propoxy}hexanenitrile수율 30%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
80 °C

실험 절차

A solution of 3-(4hydroxyphenyl)-1-propanol (2.0 g, 13.1 mmole) in DMF (5 mL) was added to a solution of DMF (35 mL) containing Nail (1.31 g, 60% in mineral oil) at 0° C. under nitrogen atmosphere. The reaction mixture was slowly warmed to 80° C. After stirring for 1 h at 80° C., the reaction mixture was cooled to 0° C., and 6-bromohexanenitrile (5.78 g,.32.83 mmole) was added. The final mixture was re-heated to 80° C., and stirred for 24 h. The reaction mixture was quenched with saturated NaCl solution (200 mL), and the product was extracted with EtOAc (300 mL). The organic layer was washed with brine solution, dried with Na2SO4, and evaporated to dryness, yielding a pale yellow solid. Purification of the crude product by flash silica column chromatography: 4/1 to 1/1 hexane/EtOAc provided 6-{3-[4-(5-cyanopentyloxy)phenyl]propoxy}hexanenitrile in 30% yield (1.33 g). Rf=0.63 in 1/1 EtOAc/hexane. 1H-NMR (CDC3, 299.96 MHz): δ (ppm) 7.09-7.07 (d, 2H), 6.81-6.78 (d, 2H), 3.96-3.92 (t, 2H), 3.42-3.37 (m, 4H), 2.64-2.58 (t, 2H), 2.39-2.32 (m, 4H), 1.87-1.52 (m, 14H).

후처리

  1. additioncontaining Nail (1.31 g, 60% in mineral oil) at 0° C. under nitrogen atmosphere
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. stirringstirred for 24 h
  4. customThe reaction mixture was quenched with saturated NaCl solution (200 mL)
  5. extractionthe product was extracted with EtOAc (300 mL)
  6. washThe organic layer was washed with brine solution
  7. dry with materialdried with Na2SO4
  8. customevaporated to dryness
  9. customyielding a pale yellow solid
  10. customPurification of the crude product by flash silica column chromatography

출처 및 근거

ORD 기록
ord-7de1b608538947cfb67a7200489897ee
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427639B2

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