Propionitrile → HCID 57470608, 화합물

HRID 602061노트

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HRID 602061 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[C@H:9]([OH:12])[CH2:10][OH:11].C(#N)CC.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:19]=[CH:18]/[C:17]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][C:3]=1[C@H:9]([OH:12])[CH2:10][OH:11]

참가 물질

8

반응물 5

HCID 7854PropionitrileHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 57470607(1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol

생성물 1

HCID 57470608HCID 57470608, 화합물수율 81%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

(1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol (2.60 g, 8.71 mmol), propionitrile (87 mL), ethyl acrylate (1.24 mL, 11.32 mmol), and triethylamine (3.6 mL, 26.13 mmol) were combined and N2 was flushed through the solution for 10 minutes. Then Pd(OAc)2 (587 mg, 0.871 mmol) and P(O-tol)3 (1.06 g, 3.48 mmol) were added and the solution was heated to 80° C. After 16 h, the solution was cooled to rt and then EtOAc was added. The solution was washed with 1N HCl (2×), brine, dried, concentrated, and purified by Biotage chromatography (0%-100% EtOAc/hexanes) to afford 1.90 g of product as an oil (81%). 1H NMR (400 MHz, chloroform-d) δ ppm 7.79 (d, J=1.77 Hz, 1 H) 7.65 (d, J=16.17 Hz, 1 H) 7.34-7.40 (m, 2 H) 6.45 (d, J=15.92 Hz, 1 H) 5.24 (ddd, J=7.39, 2.84, 2.65 Hz, 1 H) 4.27 (q, J=7.24 Hz, 2 H) 3.89-3.97 (m, 1 H) 3.57 (ddd, J=11.49, 7.45, 4.55 Hz, 1 H) 2.87 (d, J=3.28 Hz, 1 H) 2.18 (t, J=5.81 Hz, 1 H) 2.05 (s, 3 H) 1.34 (t, J=7.20 Hz, 2 H).

후처리

  1. customN2 was flushed through the solution for 10 minutes
  2. temperaturethe solution was cooled to rt
  3. washThe solution was washed with 1N HCl (2×), brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by Biotage chromatography (0%-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-daa56d881f2c41878d0c63df863066a7
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902394B2

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