3,4-dihydro-2H-pyran → HCID 68182046, 화합물

HRID 1398593노트

반응식

HRID 1398593 반응식
[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8](=[O:10])[CH3:9])[CH:4]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.CC1C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.O>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8](=[O:10])[CH3:9])[CH:4]=1

참가 물질

6

반응물 3

HCID 80803,4-dihydro-2H-pyran2회HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2회HCID 105587091-(5-(Hydroxymethyl)isoxazol-3-yl)ethanone

생성물 1

HCID 68182046HCID 68182046, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-[5-(hydroxymethyl)-1,2-oxazol-3-yl]ethanone (252 mg, 1.79 mmol), 3,4-dihydro-2H-pyran (0.24 ml, 2.68 mmol) and pyridinium 4-methylbenzenesulfonate (44.69 mg, 0.18 mmol) in DCM (10 mL) was stirred at RT for 16 hr and then for a further 0.5 hr at 40° C. after the addition of more 3,4-dihydro-2H-pyran (0.24 ml, 2.68 mmol) and pyridinium 4-methylbenzenesulfonate (44.69 mg, 0.18 mmol). The reaction mixture was diluted with water (5 ml) and the solution extracted with DCM (2×20 ml). The combined organic layers were washed with brine (5 ml), dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography (Isolute, 9:1 heptane:EtOAc) to give the title intermediate: 1H NMR (500 MHz, CDCl3) delta 1.56-1.53 (2H, m), 1.68-1.60 (2H, m), 1.89-1.69 (2H, m), 2.65 (3H, s), 3.62-3.51 (1H, m), 3.93-3.78 (1H, m), 4.68 (1H, d, J=13.9 Hz), 4.75 (1H, t, J=3.3 Hz), 4.86-4.80 (1 H, m), 6.63 (1H, s).

후처리

  1. extractionthe solution extracted with DCM (2×20 ml)
  2. washThe combined organic layers were washed with brine (5 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography (Isolute, 9:1 heptane:EtOAc)

출처 및 근거

ORD 기록
ord-89a28364f36b4a9db8f79496cff357cd
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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