Imidazole → 9-(Iodomethyl)nonadecane

HRID 628220

반응식

HRID 628220 반응식
[I:1]I.[CH2:3]([CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:12]O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[I:1][CH2:12][CH:11]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

참가 물질

7

반응물 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 214142-OctyldodecanolHCID 24437Sodium Sulfite

생성물 1

HCID 866914509-(Iodomethyl)nonadecane수율 92.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Iodine (12.25 g, 48.3 mmol) was added to a solution of 2-octyl-1-dodecanol (12.42 g, 41.6 mmol), triphenylphosphine (13.17 g, 50.2 mmol), and imidazole (3.42 g, 50.2 mmol) in 80 mL dichloromethane at 0° C. After stirring for 30 minutes, the reaction mixture was allowed to warm to room temperature over 4 hours before 12 mL of saturated Na2SO3 (aq) was added. The organics were concentrated by evaporation and the mixture taken up in 500 mL pentane, washed three times with 200 mL water, and once with 150 mL brine. The mixture was then passed through a 3 cm silica gel plug, and dried over Na2SO4. The organics were concentrated by evaporation to give a colorless oil (15.78 g, yield 92.9%). 1H NMR (CDCl3 500 MHz): δ: 2.60 (d, J=5.0 Hz, 2H), 2.00 (t, J=5.0 Hz, 1H), 1.30-1.20 (b, 32H), 0.89 (t, J=7.5 Hz, 6H); MS (EI): m/z (%) 408.23 (100) [M+]. Elemental Analysis (calc. C, 58.81; H, 10.12): found C, 58.70; H, 9.97.

후처리

  1. additionwas added
  2. concentrationThe organics were concentrated by evaporation
  3. washwashed three times with 200 mL water
  4. dry with materialdried over Na2SO4
  5. concentrationThe organics were concentrated by evaporation

출처 및 근거

ORD 기록
ord-3824af1174994d87889bc1a111ee3b6b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09312492B2

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