N,N,N',N'-Tetramethylethylenediamine → 1-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-(2-methoxymethyloxyethyl)phenyl]pentane

HRID 1588140ノート

反応式

HRID 1588140 の反応式
[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][C:7]1[C:12]([O:13][CH2:14][O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=[C:9]([O:19][CH2:20][O:21][CH3:22])[C:8]=1[O:23][CH3:24].CN(C)CCN(C)C.C([Li])CCC.I[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]1[C:49]([O:50][CH2:51][O:52][CH3:53])=[C:48]([O:54][CH3:55])[CH:47]=[C:46]([O:56][CH2:57][O:58][CH3:59])[C:45]=1[O:60][CH3:61]>C1(C)C=CC=CC=1.CN(C)P(=O)(N(C)C)N(C)C.C(OCC)C>[CH3:61][O:60][C:45]1[C:46]([O:56][CH2:57][O:58][CH3:59])=[CH:47][C:48]([O:54][CH3:55])=[C:49]([O:50][CH2:51][O:52][CH3:53])[C:44]=1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][C:10]1[C:9]([O:19][CH2:20][O:21][CH3:22])=[C:8]([O:23][CH3:24])[C:7]([CH2:6][CH2:5][O:4][CH2:3][O:2][CH3:1])=[C:12]([O:13][CH2:14][O:15][CH3:16])[C:11]=1[O:17][CH3:18]

参加物

8

反応物 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 197571521-Methoxymethoxy-2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethaneHCID 197572171-(5-Iodopent-1-yl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzeneHCID 178418339Butyllithium

生成物 1

HCID 197572501-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-(2-methoxymethyloxyethyl)phenyl]pentane

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒2 回HCID 3283Diethyl Ether溶媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
-78 °C

実験手順

1.0 Gram of 1-methoxymethoxy-2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethane was dissolved in a mixed solvent of 20 ml of toluene with 5 ml of hexamethylphosphoric triamide, to this solution was added 0.52 ml of N,N,N',N'-tetramethylethylenediamine and the whole mixture was cooled to -78° C. in a dry ice-acetone bath, then 2.7 ml of n-butyllithium (1.6 mole solution) was added dropwise to the reaction mixture. 15 Minutes later, a solution prepared by dissolving 1.56 g of 1-(5-iodopent-1-yl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene in 12 ml of toluene was added to the reaction mixture, and the temperature of the reaction mixture was gradually elevated to room temperature and the reaction mixture was stirred further for 4 hours. 50 Milliliters of diethyl ether was added to the reaction mixture, and the organic layer was washed with water, and with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate. After concentration, the residue thus obtained was purified by means of a silica gel column chromatography (diameter 3 cm×length 10 cm, Merck, eluent: 30% ethyl acetate-n-hexane) to obtain 2.1 g of 1-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-(2-methoxymethyloxyethyl)phenyl]pentane. Amorphous powdery substance.

後処理

  1. custom15 Minutes later, a solution prepared
  2. additionwas added to the reaction mixture
  3. customwas gradually elevated to room temperature
  4. washthe organic layer was washed with water
  5. dry with materialwith a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate
  6. concentrationAfter concentration
  7. customthe residue thus obtained
  8. customwas purified by means of a silica gel column chromatography (diameter 3 cm×length 10 cm, Merck, eluent: 30% ethyl acetate-n-hexane)

出典と根拠

ORDレコード
ord-c4cd6510fa1e4078a81c7c4b8996c2ac
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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