Water → HCID 86748241, 화합물

HRID 2379530

반응식

HRID 2379530 반응식
C([Li])CCC.[CH2:6]([O:13][CH2:14][O:15][CH2:16][Sn](CCCC)(CCCC)CCCC)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:30]/[C:31](/[CH2:35][CH2:36]/[CH:37]=[C:38](\[CH3:45])/[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])=[CH:32]\[CH2:33]Br.O>C1COCC1>[CH3:30]/[C:31](/[CH2:35][CH2:36]/[CH:37]=[C:38](\[CH3:45])/[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])=[CH:32]\[CH2:33][CH2:16][O:15][CH2:14][O:13][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 5366048(2E,6E)-1-bromo-3,7,11-trimethyldodeca-2,6,10-trieneHCID 11048467(Benzyloxymethoxy)methyl-tri-(n-butyl) tinHCID 178418339Butyllithium

생성물 1

HCID 86748241HCID 86748241, 화합물수율 54.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

n-Butyl lithium (1.6M in hexane, 8.6 mL, 13.8 mmol) was added under nitrogen to a stirred solution of (benzyloxymethoxy)methyl-tri-(n-butyl) tin (6.1 g, 13.8 mmol) in THF (56 mL) at -78° C. The resulting mixture was stirred at -78° C. for 10 min, then added a solution of (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienylbromide (3.5 g, 12.3 mmol) in THF (4 mL) via a dropping funnel. The resulting mixture was stirred at -78° C. for 0.5 hours, then poured into cold water and extracted with ether. The ethereal extract was dried, filtered and evaporated to afford a residue, which was purified by flash chromatography on a silica gel column. Elution of the column with hexane:ether (25:1, v:v) provided the title compound as a colorless oil (2.39 g, 6.7 mmol, 54.5%).

후처리

  1. stirringThe resulting mixture was stirred at -78° C. for 0.5 hours
  2. extractionextracted with ether
  3. extractionThe ethereal extract
  4. customwas dried
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a residue, which
  8. customwas purified by flash chromatography on a silica gel column
  9. washElution of the column with hexane:ether (25:1, v:v)

출처 및 근거

ORD 기록
ord-7ed07afb4d4b43f2ab4d18e4098f9c92
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05362906

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