Acetic Anhydride → HCID 9895874, 화합물

HRID 1954273노트

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HRID 1954273 반응식
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:36]=[C:35]([CH3:37])[C:20]([O:21][S:22]([C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[C:27]([OH:34])[CH:26]=3)(=[O:24])=[O:23])=[C:19]([CH3:38])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:39](OC(=O)C)(=[O:41])[CH3:40].[I-].[Mg+2].[I-]>C(OCC)C>[C:39]([O:34][C:27]1[CH:26]=[C:25]([S:22]([O:21][C:20]2[C:35]([CH3:37])=[CH:36][C:17]([C:9]3[C:10]4[C:14]([CH3:15])=[C:13]([CH3:16])[S:12][C:11]=4[C:2]([Br:1])=[C:3]4[C:8]=3[CH:7]=[CH:6][CH:5]=[CH:4]4)=[CH:18][C:19]=2[CH3:38])(=[O:24])=[O:23])[CH:33]=[CH:32][C:28]=1[C:29]([OH:31])=[O:30])(=[O:41])[CH3:40]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 5462737Magnesium diiodideHCID 9960530HCID 9960530, 화합물

생성물 1

HCID 9895874HCID 9895874, 화합물수율 76%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A stirred suspension containing 4-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-2-hydroxy-benzoic acid (0.350 g, 0.572 mmol), acetic anhydride (4.55 mL) and magnesium iodide (0.159 g, 0.572 mmol) in anhydrous ethyl ether (10.0 mL, 0.05M) was refluxed for 0.5 h. The reaction was cooled to ambient temperature, quenched with H2O (150 mL), extracted with ether and concentrated. The crude product was dissolved in THF:H2O (1:1, 10 mL) and refluxed for 1 h. The reaction was cooled to ambient temperature, diluted with H2O (50 mL) and extracted with ether and EtOAc. The combined organic extracts were concentrated and purified on 2% H3PO4 /MeOH treated silica gel, eluting with a 20 & 25% EtOAc/pet. ether step gradient to give 0.298 g (76%) of the title compound as a white solid; 1H NMR (DMSO-d6) δ 1.58 (s, 3 H), 2.15 (s, 6 H), 2.30 (s, 3 H), 2.45 (s, 3 H), 7.20 (s, 2 H), 7.46-7.54 (m, 2 H), 7.67 (t, 1 H), 7.94 (d, 1 H), 8.05 (dd, 1 H), 8.20-8.25 (m, 2 H), 13.75-13.95 (br.s., 1 H). mass spectrum (-ESI), m/z 651/653 (M-H).

후처리

  1. temperaturewas refluxed for 0.5 h
  2. customquenched with H2O (150 mL)
  3. extractionextracted with ether
  4. concentrationconcentrated
  5. dissolutionThe crude product was dissolved in THF:H2O (1:1, 10 mL)
  6. temperaturerefluxed for 1 h
  7. temperatureThe reaction was cooled to ambient temperature
  8. additiondiluted with H2O (50 mL)
  9. extractionextracted with ether and EtOAc
  10. concentrationThe combined organic extracts were concentrated
  11. custompurified on 2% H3PO4 /MeOH
  12. additiontreated silica gel
  13. washeluting with a 20 & 25% EtOAc/pet. ether step gradient

출처 및 근거

ORD 기록
ord-0ae01d51572c46709a75a169c7d0510d
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06121271

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