Tetrahydrofuran → 2-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl 3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl ether

HRID 1588153ノート

反応式

HRID 1588153 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[C:9]([O:10][CH2:11][O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=[C:6]([O:16][CH2:17][O:18][CH3:19])[C:5]=1[O:20][CH3:21].[H-].[Na+].O1CCCC1.I[CH2:30][CH2:31][CH2:32][C:33]1[C:38]([O:39][CH2:40][O:41][CH3:42])=[C:37]([O:43][CH3:44])[CH:36]=[C:35]([O:45][CH2:46][O:47][CH3:48])[C:34]=1[O:49][CH3:50]>CN(C)C=O.C(OCC)C>[CH3:50][O:49][C:34]1[C:35]([O:45][CH2:46][O:47][CH3:48])=[CH:36][C:37]([O:43][CH3:44])=[C:38]([O:39][CH2:40][O:41][CH3:42])[C:33]=1[CH2:32][CH2:31][CH2:30][O:1][CH2:2][CH2:3][C:4]1[C:9]([O:10][CH2:11][O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=[C:6]([O:16][CH2:17][O:18][CH3:19])[C:5]=1[O:20][CH3:21]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 137145691-(2-Hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzeneHCID 197572441-(3-Iodopropyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene

生成物 1

HCID 197572532-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl 3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl ether

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

374 Milligrams of 1-(2-hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene was dissolved in 3 ml of dimethylformamide, under ice-cooling conditions, 80 mg of sodium hydride (60% dispersion) was added thereto, then 2 ml of tetrahydrofuran solution containing 527 mg of 1-(3-iodopropyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene was added. The reaction mixture was heated at 50° C. in an oil bath. 6 Hours later, ice water and 100 ml of diethyl ether were added to the reaction mixture. The ether layer was washed twice with 50 ml of water, then washed twice with 50 ml of a saturated sodium chloride aqueous solution, then dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the residue obtained was purified by means of a silica gel column chromatography (diameter 3 cm×length 15 cm, eluent: 40% ethyl acetate-n-hexane mixed solvent, adsorbent: "Wakogel C-200") to obtain 484 mg of 2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl 3 -[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl ether.

後処理

  1. additionwas added
  2. additionwas added
  3. washThe ether layer was washed twice with 50 ml of water
  4. washwashed twice with 50 ml of a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThis solution was concentrated under reduced pressure
  7. customthe residue obtained
  8. customwas purified by means of a silica gel column chromatography (diameter 3 cm×length 15 cm, eluent: 40% ethyl acetate-n-hexane mixed solvent, adsorbent: "Wakogel C-200")

出典と根拠

ORDレコード
ord-9b083a2a6b98427abb4af477927e812d
出典データセット
uspto-grants-1993_06
特許番号
US05220042

反応ノート

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