2-(Tributylstannyl)furan → 2-(6-Methoxy-1-methoxymethoxy-3-methyl-naphthalen-2-yl)-furan

HRID 1992969노트

반응식

HRID 1992969 반응식
C([Sn](CCCC)(CCCC)[C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)CCC.Br[C:20]1[C:29]([CH3:30])=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:31][CH3:32])[CH:26]=2)[C:21]=1[O:33][CH2:34][O:35][CH3:36]>C1(C)C=CC=CC=1.CCOCC.O.C1(P([Pd-4](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)C=CC=CC=1>[CH3:32][O:31][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[C:21]([O:33][CH2:34][O:35][CH3:36])=[C:20]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[C:29]([CH3:30])=[CH:28]2

참가 물질

7

반응물 2

HCID 43936882-(Tributylstannyl)furanHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene2회

생성물 1

HCID 685396222-(6-Methoxy-1-methoxymethoxy-3-methyl-naphthalen-2-yl)-furan수율 76%

시약·촉매·용매 4

HCID 178420553HCID 178420553, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
105 °C

실험 절차

2-(Tributylstannyl)-furan (0.4 mL, 1.29 mmol)) was added slowly to a solution of 2-bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene (14 (0.4 g, 1.29 mmol) in toluene (10 mL). Reaction mixture was heated at 105° C. A portion (0.01 g) of tetrakis(triphenylphosphino)palladium (0) (0.061 g, 0.053 mmol) was added every 1 h until reaction was complete. Reaction mixture was cooled to RT then diluted with Et2O and water. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude oil was purified with a gradient of 20% EtOAc in hexanes to give 0.29 g (76%) of the title compound (213) as oil. 1H NMR (400 MHz, d-CDCl3): δ 2.36 (s, 3H), 3.37 (s, 3H), 3.93 (s, 3H), 4.85 (s, 2H), 6.49-6.50 (m, 1H), 6.53-6.55 (m, 1H), 7.05 (m, 1H), 7.11 (dd, J1=2.4 Hz, J2=9.2 Hz, 1H), 7.39 (s, 1H), 7.58-7.58 (m, 1H), 8.08 (d, J=9.2 Hz, 1H).

후처리

  1. customReaction mixture
  2. customReaction mixture
  3. temperaturewas cooled to RT
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude oil was purified with a gradient of 20% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-9bf772612e05454888232bcbc75a2c9e
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649093B2

반응 노트

불러오는 중…