Triethylamine → HCID 22392428, 화합물

HRID 353001

반응식

HRID 353001 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

HCID 22392428HCID 22392428, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6ecf0719a3404b7cb6bc1ac809bd0f88
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06749771B1

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