Ammonium Chloride → (6R)-2,6-Dimethylnon-2-ene

HRID 28426

反応式

HRID 28426 の反応式
[CH2:1](Br)[CH2:2][C@H:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH3:4].[Li+].[Cl-].[CH3:14][Mg]Cl.[Cl-].[NH4+]>C1COCC1>[CH3:9][C:8](=[CH:7][CH2:6][CH2:5][C@H:3]([CH3:4])[CH2:2][CH2:1][CH3:14])[CH3:10]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 10900106(S)-(+)-Citronellyl bromideHCID 178418332HCID 178418332、化合物

生成物 1

HCID 15345839(6R)-2,6-Dimethylnon-2-ene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To (S)-citronellyl bromide (50 g, 0.228 mol) in THF (800 mL) at 0° C. was added LiCl (4.3 g) followed by CuCl2 (6.8 g). After 30 minutes methylmagnesium chloride (152 mL of a 3 M solution in THF, Aldrich) was added and the solution warmed to room temperature. After 10 hours the solution was cooled to 0° C. and a saturated aqueous solution of ammonium chloride carefully added. The resultant two layers were separated and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4) and concentrated to give (R)-2,6-dimethyl-non-2-ene. 32.6 g; 93%. Used without further purification. 1H NMR(400 MHz; CDCl3) δ 5.1 (m, 1H), 1.95 (m, 2H), 1.62 (s, 3H), 1.6 (s, 3H), 1.3 (m, 4H), 1.2 (m, 2H), 0.8 (s, 6H);13C NMR (100 MHz; CDCl3) 131.13, 125.28, 39.50, 37.35, 32.35, 25.92, 25.77, 20.31, 19.74, 17.81, 14.60.

後処理

  1. temperatureAfter 10 hours the solution was cooled to 0° C.
  2. customThe resultant two layers were separated
  3. extractionthe aqueous phase extracted with ether
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-ddc9d6f6ae4348f4999a22f5dc4af579
出典データセット
uspto-grants-2008_09
特許番号
US07419981B2

関連ノート

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