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

HRID 1992969ノート

反応式

HRID 1992969 の反応式
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

参加物

7

反応物 2

HCID 43936882-(Tributylstannyl)furanHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene2 回

生成物 1

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

試薬・触媒・溶媒 4

HCID 178420553HCID 178420553、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
105 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9bf772612e05454888232bcbc75a2c9e
出典データセット
uspto-grants-2010_01
特許番号
US07649093B2

反応ノート

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