Water → 2',3,3',4,4',5-Hexamethoxybenzophenone

HRID 1836801ノート

反応式

HRID 1836801 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH3:13].C([Li])CCC.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:24](Cl)=[O:25].O>O1CCCC1>[CH3:13][O:12][C:3]1[C:4]([O:10][CH3:11])=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[C:24](=[O:25])[C:23]1[CH:22]=[C:21]([O:20][CH3:19])[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=1

参加物

6

反応物 4

HCID 962WaterHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 2569301-Bromo-2,3,4-trimethoxybenzeneHCID 178418339Butyllithium

生成物 1

HCID 234999892',3,3',4,4',5-Hexamethoxybenzophenone収率 20.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of bromobenzene 9 (0.21 g) in dry tetrahydrofuran (5 mL) cooled to −78° C. was added n-butyl lithium (0.38 mL, 2.5 M, 1.1 eq.). The solution was stirred for 30 min. and 3,4,5-trimethoxybenzoyl chloride (0.2 g) in anhydrous tetrahydrofuran was added. The resulting solution was then stirred for an additional 28 hours. The reaction was stopped with water, extracted with ethyl acetate and the solvent removed (in vacuo) to give a yellow oil. Separation by flash column chromatography (hexane-ethyl acetate, 3:1) afforded a colorless solid (0.06 g, 20.5%). The solid was recrystallized twice from ethyl acetate-hexane: m.p. 124.6-125.9° C., lit22 m.p. 121° C.; EIMS m/z 362 (M+), 345, 317, 181, 169, 151; 1H NMR δ 7.11 (1H, d, J=9.0 Hz, H6), 7.08 (2H, s, H2,6), 6.72 (1H, d, J=9.0 Hz, H5′), 3.94 (3H, s, OCH3), 3.93 (3H, s, OCH3), 3.90 (3H, s, OCH3), 3.85 (6H, s, OCH3,3,5), 3.80 (3H, s, OCH3).

後処理

  1. stirringThe resulting solution was then stirred for an additional 28 hours
  2. extractionextracted with ethyl acetate
  3. customthe solvent removed (in vacuo)
  4. customto give a yellow oil
  5. customSeparation by flash column chromatography (hexane-ethyl acetate, 3:1)

出典と根拠

ORDレコード
ord-1394388b14f14d2a8e5d5b8f4b89a66f
出典データセット
uspto-grants-2004_08
特許番号
US06777578B2

反応ノート

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