Ammonium Chloride → 3,7,11-Trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol

HRID 5661

反応式

HRID 5661 の反応式
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:21])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].[CH:22]([Mg]Br)=[CH2:23].[Cl-].[NH4+]>O1CCCC1>[CH3:7][C:6]([OH:8])([CH2:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:21])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[CH:22]=[CH2:23]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 539858946,10-Dimethyl-11-(2-tetrahydropyranyl)oxy-5,9-undecadien-2-oneHCID 178418507HCID 178418507、化合物

生成物 1

HCID 678485313,7,11-Trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (80 mg, 0.27 mmol) in tetrahydrofuran (3 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (0.3 ml, 0.3 mmol, 1.0 M), and the mixture was warmed to room temperature and stirred for 10 hours. After addition of saturated aqueous ammonium chloride (2 ml), the reaction mixture was extracted with ether. The extract was dried over Na2SO4 and evaporated in vacuo to remove the solvent to give a crude product, which was purified with silica gel column chromatography to obtain 3,7,11-trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol (61 mg, 70%). IR(film)cm-1 ; 3460, 2950, 2880, 1200, 1118, 1075, 1022, 905, 865, 810.

後処理

  1. extractionthe reaction mixture was extracted with ether
  2. dry with materialThe extract was dried over Na2SO4
  3. customevaporated in vacuo
  4. customto remove the solvent
  5. customto give a crude product, which
  6. customwas purified with silica gel column chromatography

出典と根拠

ORDレコード
ord-040d953b7c4342fe86b15659471a5179
出典データセット
uspto-grants-1993_09
特許番号
US05245085

関連ノート

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