Allyltributylstannane → 4-Allylnaphthalene-1-carboxylic acid methyl ester

HRID 1814374노트

반응식

HRID 1814374 반응식
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](Br)=[CH:7][CH:6]=1)=[O:4].[CH2:16]([Sn](CCCC)(CCCC)CCCC)[CH:17]=[CH2:18]>C1(C)C=CC=CC=1.CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:18][CH:17]=[CH2:16])=[CH:7][CH:6]=1)=[O:4]

참가 물질

6

반응물 2

HCID 90628AllyltributylstannaneHCID 22711886Methyl 4-bromo-1-naphthoate

생성물 1

HCID 696928344-Allylnaphthalene-1-carboxylic acid methyl ester수율 89%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
120 °C

실험 절차

To a solution of 4-bromo-naphthalene-1-carboxylic acid methyl ester (2.0 g, 7.9 mmol) in toluene (20 mL) was added allyltributyltin (2.7 mL), tetrakis(triphenylphosphine)palladium(0) (183 mg, 0.16 mmol) and 2 crystals of BHT. The system was purged under vacuum and nitrogen and allowed to heat to 120° C. under N2 for 4 h. TLC analysis (silica, 1:1 ethyl acetate-hexanes) showed the reaction to be completed with only one new fluorescent spot present. The mixture was diluted with ether, washed with H2O, 10% HCl, and then saturated sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (SiO2, 9:1 hexanes-ether) to give (1.6 g, 89%) 4-allylnaphthalene-1-carboxylic acid methyl ester as a colorless liquid. MS m/z 227.1 (M+1). 1H NMR (400 mHz) CDCl3 8.95(d 1H), 8.11(d, 1H), 8.08(d, 1H), 7.58(m, 2H), 7.37(d, 1H), 6.09(m, 1H), 5.11(m, 2H), 3.99(s, 3H), 3.88(d, 2H).

후처리

  1. customThe system was purged under vacuum and nitrogen
  2. customthe reaction
  3. washwashed with H2O, 10% HCl
  4. dry with materialsaturated sodium bicarbonate, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography (SiO2, 9:1 hexanes-ether)

출처 및 근거

ORD 기록
ord-26d834d3d340400aba3e64ce00786ee8
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875765B2

반응 노트

불러오는 중…