Imidazole → 9-(Iodomethyl)nonadecane

HRID 628220

反応式

HRID 628220 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 866914509-(Iodomethyl)nonadecane収率 92.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3824af1174994d87889bc1a111ee3b6b
出典データセット
uspto-grants-2016_04
特許番号
US09312492B2

関連ノート

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