Epichlorohydrin → HCID 76010298, 화합물

HRID 1157977노트

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HRID 1157977 반응식
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6](=[O:17])[CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>CN(C)C=O>[O:26]1[CH2:25][CH:24]1[CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:17])[CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 97793HCID 97793, 화합물2회

생성물 1

HCID 76010298HCID 76010298, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a well-stirred solution of 4′-hydroxy-4-methoxy-chalcone, 7 (15 g, 59 mmol) in dry dimethyl formamide (170 mL) was added 50% sodium hydride (5.6 g, 236 mmol) at 0-5° C. and after 30 minutes, excess of epichlorohydrin (13.8 mL, 177 mmol) was added and stirred at room temperature for overnight. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with chloroform. The combined organic layers were dried over sodium sulphate, filtered and evaporated to dryness. The crude product was purified by column chromatography to afford 13. Yield 11 g (60%); mp 85-87° C.; MS (FAB) 311 (M++1); IR (KBr) 1655; 1H NMR (200 MHz, CDCl3) δ 8.02 (d, J=8.8 Hz, 2H), 7.77 (d, J=15.6 Hz, 1H), 7.59 (d, J=8.7 Hz, 2H), 7.41 (d, J=15.6 Hz, 1H), 6.99 (d, J=8.8 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 4.32 (dd, J=11.1 Hz, 2.9 Hz, 1H), 4.01 (dd, J=11.1 Hz, 5.7 Hz, 1H), 3.84 (s, 31H), 3.40-3.35 (m, 1H), 2.92 (t, J=4.5 Hz, 4.5 Hz, 1H), 2.77 (dd, J=4.8 Hz, 2.6 Hz, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-1aed249538c84b8b95abdd0a95581614
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807712B2

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