1,2-Dimethoxyethane → 3-(6-Methoxy-1-(methoxymethoxy)-3-methyl-naphthalen-2-yl)-thiophene

HRID 1992961ノート

反応式

HRID 1992961 の反応式
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[C:3]=1[O:15][CH2:16][O:17][CH3:18].[S:19]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20]1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(OCC)C.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>[CH3:14][O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3]([O:15][CH2:16][O:17][CH3:18])=[C:2]([C:21]1[CH:22]=[CH:23][S:19][CH:20]=1)[C:11]([CH3:12])=[CH:10]2

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene

生成物 1

HCID 685377683-(6-Methoxy-1-(methoxymethoxy)-3-methyl-naphthalen-2-yl)-thiophene

試薬・触媒・溶媒 2

HCID 178420553HCID 178420553、化合物触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
160 °C

実験手順

2-bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene (14) (0.35 g, 1.12 mmol), thiophene 3-boronic acid (0.359 g, 2.81 mmol), tetrakis(triphenylphosphino)palladium (0) (0.031 g, 0.027 mmol), 2 M sodium carbonate (4 mL) and ethylene glycol dimethyl ether (4 mL) were added in a sealed tube and heated at 160° C. for 20 min. Reaction mixture was cooled to room temperature then diluted with diethyl ether. The mixture was washed with water followed by brine, dried over Na2SO4, filtered and concentrated. The crude material purified with a gradient of 1% EtOAc to 4% EtOAc in hexanes over 45 min to afford the title compound (199) as oil, 0.347 g, (98%). 1H NMR (400 MHz, d-CDCl3): δ 2.29 (s, 3H), 3.23 (s, 3H), 3.93 (s, 3H), 4.76 (s, 2H), 7.06-7.07 (m, 1H), 7.10-7.15 (m, 2H), 7.25-7.26 (m, 1H), 7.40-7.42 (m, 2H), 8.04 (d, J=9.2 Hz, 1H).

後処理

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. washThe mixture was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material purified with a gradient of 1% EtOAc to 4% EtOAc in hexanes over 45 min

出典と根拠

ORDレコード
ord-f53bd4d571a94fd2a825ec539686163f
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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