Triethylamine → HCID 22392428、化合物

HRID 353001

反応式

HRID 353001 の反応式
S(Cl)(C)(=O)=O.[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(=[O:9])[CH:7]=[CH2:8].O[C:28]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][C:29]=1[CH:30]=[O:31].[C:37]([O-:40])(O)=[O:38].[Na+].C(N([CH2:47][CH3:48])CC)C>C1COCC1.CN(C1C=CN=CC=1)C>[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][C:28]2[CH:35]=[CH:34][C:33]([O:36][C:22]([C:21]3[CH:25]=[CH:26][C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:40][C:37](=[O:38])[CH:47]=[CH2:48])=[CH:19][CH:20]=3)=[O:23])=[CH:32][C:29]=2[CH:30]=[O:31])=[O:23])=[CH:25][CH:26]=1)(=[O:9])[CH:7]=[CH2:8]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 709492,5-DihydroxybenzaldehydeHCID 516892Sodium BicarbonateHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

生成物 1

HCID 22392428HCID 22392428、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-25 °C

実験手順

A solution of mesylchloride (4.23 g, 36.94 mmol) in 10 ml of dry THF was added dropwise under argon over a period of 15 minutes to a cooled (−25 ° C.) solution of 4-(6-acryloyloxyhexyloxy)benzoic acid and triethylamine (20 ml) in 80 ml of dry THF. The reaction mixture was then stirred for 60 min at −25 ° C., treated with a solution of 2,5-dihydroxybenzaldehyde (2.3 g, 16.65 mmol) in 60 ml of dry THF containing 195 mg of DMAP and further stirred at −25° C. for 2 h. The reaction mixture was then allowed to warm to room temperature and stirring was continued overnight. The reaction mixture was then poured into 120 ml of saturated NaHCO3 and extracted with 2×200 ml of ether. The combined organic extracts were washed with 3N HCl (200 ml) and semi-saturated NaCl solution (2×100 ml), dried over MgSO4, filtered and dried to give a slightly yellow pasty material. This was purified by flash chromatography over a short silica column (CH2Cl2/Et2O:19.5/0.5) to give a white residue (9.25 g) which was dissolved in CH2Cl2 (25 ml) then recrystallised from ethanol (250 ml) to give pure 2,5-di-[4-(6-acryloyloxy-hexyloxy)hexyloxy)phenylcarbonyloxy]benzaldehyde as a white crystalline material. Yield 8.5 g.

後処理

  1. stirringfurther stirred at −25° C. for 2 h
  2. temperatureto warm to room temperature
  3. stirringstirring
  4. waitwas continued overnight
  5. extractionextracted with 2×200 ml of ether
  6. washThe combined organic extracts were washed with 3N HCl (200 ml) and semi-saturated NaCl solution (2×100 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customdried
  10. customto give a slightly yellow pasty material
  11. customThis was purified by flash chromatography over a short silica column (CH2Cl2/Et2O:19.5/0.5)

出典と根拠

ORDレコード
ord-6ecf0719a3404b7cb6bc1ac809bd0f88
出典データセット
uspto-grants-2004_06
特許番号
US06749771B1

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