2,4,6-Trimethylpyridine → Geranyl chloride

HRID 22203

반응식

HRID 22203 반응식
[CH3:1]/[C:2](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3]\[CH2:4]O.N1C(C)=CC(C)=CC=1C.[Cl-:21].[Li+]>CN(C=O)C.CS(Cl)(=O)=O>[Cl:21][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10]

참가 물질

6

반응물 3

HCID 79532,4,6-TrimethylpyridineHCID 433294Lithium ChlorideHCID 637566Geraniol

생성물 1

HCID 6372219Geranyl chloride수율 89.4%

시약·촉매·용매 2

HCID 31297Methanesulfonyl chloride촉매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 30.0 g (0.194 mol) of (E)-3,7-dimethyl-2,6-octadien-1-ol and 28.27 mL (0.213 mol) of 2,4,6-collidine under argon at room temperature was added dropwise 8.23 g (0.194 mol) of lithium chloride in 100 mL of DMF. The mixture was cooled to 0° C. and treated with 16.56 mL (0.213 mmol) of methanesulfonyl chloride dropwise over 10 minutes. The reaction was stirred at 0° C. for 1.5 hours (solid present), then was poured into 500 mL of ice/water. The aqueous solution was washed three times with 200 mL portions of hexane, the organic layers were combined and washed with 5% KHSO4, water, NaHCO3, brine, dried (MgSO4) and evaporated to provide 29.95 g of a pale yellow oil. Rapid flash chromatography was performed on 400 g of silica gel, eluting with 3:9 EtOAc/hexane. Pure product fractions were combined and evaporated to provide 25.20 g (75%) of title compound as a pale yellow oil.

후처리

  1. washThe aqueous solution was washed three times with 200 mL portions of hexane
  2. washwashed with 5% KHSO4, water, NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-47007e2562b24ef99dd6e8e5a647b415
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428028

연결된 노트

불러오는 중…