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

HRID 1836801노트

반응식

HRID 1836801 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 234999892',3,3',4,4',5-Hexamethoxybenzophenone수율 20.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1394388b14f14d2a8e5d5b8f4b89a66f
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777578B2

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