Cyclododecanecarboxaldehyde → 1-(3-Phenyl-1-propenyl)cyclododecane

HRID 37305

반응식

HRID 37305 반응식
[Br-].[C:2]1([CH2:8][CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH:34]1([CH:46]=O)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>CCOCC>[C:2]1([CH2:8][CH:9]=[CH:46][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 78737CyclododecanecarboxaldehydeHCID 10863251Phenethyltriphenylphosphonium bromideHCID 178418339Butyllithium

생성물 1

HCID 544717161-(3-Phenyl-1-propenyl)cyclododecane수율 88.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

To 11.4 g (25.5 mmol) of phenylethyl triphenylphosphonium bromide in 50 mL of dry ether at 0° C. is added 10.2 mL (25.5 mmol) of 2.5M butyllithium. The suspension is stirred at 0° C. for 1 hour followed by the addition of 5.0 g (25.5 mmol) of cyclododecane carboxaldehyde. The mixture is stirred at room temperature for 3 hours after which time no starting material is evident by TLC. The reaction mixture is quenched with 1N HCl. The layers are separated and the aqueous layer is washed twice with ethyl ether. The combined organic layers are dried over a MgSO4 and the ether is evaporated. The residue is flash chromatographed on silica gel using hexanes to give 6.4 g of a colorless oil: NMR (CDCl3) δ 1.0-1.6 (m, 10H), 2.6 (m, 1H), 3.4 (d, 2H, J=8 Hz, ), 5.3 (t, 1H, J=7 Hz), 5.45 (q, 1H, J=7 Hz), 7.2 ppm (m, 5H).

후처리

  1. stirringThe mixture is stirred at room temperature for 3 hours after which time no starting material
  2. customThe reaction mixture is quenched with 1N HCl
  3. customThe layers are separated
  4. washthe aqueous layer is washed twice with ethyl ether
  5. dry with materialThe combined organic layers are dried over a MgSO4
  6. customthe ether is evaporated
  7. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-3a39a55380c9432ea51b387bb28c73e5
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420153

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