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Sodium Iodide → 1,4-Dimethoxy-2,5-bis(methoxymethoxy)-3-(4-nonynyl)benzene

HRID 1588170
ノート
印刷プレビュー

反応式

HRID 1588170 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH2:16][O:17][CH3:18].C([Li])(CC)C.Br[CH2:25][CH2:26][CH2:27][C:28]#[C:29][CH2:30][CH2:31][CH2:32][CH3:33].[I-].[Na+]>O1CCCC1.C(OCC)(=O)C.CCCCCC.C1C=CC=CC=1.C(OCC)C.CN(C)P(=O)(N(C)C)N(C)C>[CH3:14][O:13][C:6]1[CH:5]=[C:4]([O:15][CH2:16][O:17][CH3:18])[C:3]([O:2][CH3:1])=[C:8]([CH2:25][CH2:26][CH2:27][C:28]#[C:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:7]=1[O:9][CH2:10][O:11][CH3:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 5238Sodium IodideHCID 10061046HCID 10061046、化合物HCID 109765551-Bromo-4-nonyneHCID 178418400CID 53628100

生成物 1

HCID 197571921,4-Dimethoxy-2,5-bis(methoxymethoxy)-3-(4-nonynyl)benzene

試薬・触媒・溶媒 4

HCID 8028Tetrahydrofuran溶媒
HCID 12679
Hexamethylphosphoramide
溶媒
HCID 21226206Ethyl acetate hexane溶媒
HCID 22174802Benzene ether溶媒

反応条件

温度
-78 °C

実験手順

3.0 Grams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in 500 ml of anhydrous tetrahydrofuran, this solution was cooled to -78° C. on a dry ice-acetone bath under an atmosphere of argon gas. To this solution was added dropwise 10.7 ml of secbutyllithium (1.3M cyclohexane solution), and stirred for 30 minutes. Then 3.54 g of 1-bromo-4-nonyne was added dropwise thereto, further 2.1 g of sodium iodide and 60 ml of hexamethylphosphoric triamide were added to the reaction mixture and stirred for 12 hours at room temperature. Tetrahydrofuran was removed under reduced pressure, then to the residue obtained was added 300 ml of mixed solvent of benzene-diethyl ether (1:1). The organic layer was washed four times with 100 ml of water, and washed four times with 100 ml of a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate then the solvent was removed under reduced pressure. The residue obtained was treated by means of a silica gel column chromatography (diameter: 5.5 cm×length 15.5 cm, "Wakogel C-200", developing and eluting solvent: 20% ethyl acetate-n-hexane). There was obtained 1.4 g of 1,4-dimethoxy-2,5-bis(methoxymethoxy)-3-(4-nonynyl)benzene as in the form of colorless oily substance.

後処理

  1. stirringstirred for 12 hours at room temperature
  2. customTetrahydrofuran was removed under reduced pressure
  3. customto the residue obtained
  4. washThe organic layer was washed four times with 100 ml of water
  5. washwashed four times with 100 ml of a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue obtained

出典と根拠

ORDレコード
ord-7b87cfbfbbf446aa9a473991a5466dbd
出典データセット
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05220042

反応ノート

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