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

HRID 5661

반응식

HRID 5661 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-040d953b7c4342fe86b15659471a5179
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245085

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