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Potassium Carbonate → HCID 57545169, 화합물

HRID 1661521
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HRID 1661521 반응식
[I-].[I-].[Sm+2].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C@:11]2([C@H:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:28][CH:29]=[O:30])[C:15](=[O:16])[C:14]3[C:17]([O:24][CH2:25][CH3:26])=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[CH:20][C:13]=3[O:12]2)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C@:11]23[C@H:27]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:28][C@H:29]([OH:30])[C@@:15]2([OH:16])[C:14]2[C:17]([O:24][CH2:25][CH3:26])=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[CH:20][C:13]=2[O:12]3)=[CH:7][CH:6]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 57545213HCID 57545213, 화합물HCID 178506586HCID 178506586, 화합물

생성물 1

HCID 57545169HCID 57545169, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

178 ml (17.9 mmol) of a 0.1 M solution of samarium diiodide in THF is cooled to 0° C. under argon, and a solution of 2.60 g (5.10 mmol) of (S*,R*)-3-[2-(4-bromophenyl)-4,6-diethoxy-3-oxo-2,3-dihydrobenzofuran-2-yl]-3-phenylpropanal in 30 ml of degassed THF is added dropwise. The mixture is stirred at 0° C. for 1 h and at RT for 1 h. An ice-cold saturated sodium potassium tartrate solution with 10% potassium carbonate is added, the phases are separated, the aqueous phase is extracted three times with dichloromethane, and the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Column chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 95:5) results in 1.55 g (58% of theory) of the product as racemic mixture.

후처리

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted three times with dichloromethane
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customColumn chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 95:5) results in 1.55 g (58% of theory) of the product as racemic mixture

출처 및 근거

ORD 기록
ord-a5358a944746455a863d7726f9042285
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030347B2

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