Water → HCID 178489287, 화합물

HRID 45429

반응식

HRID 45429 반응식
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](/[C:9](=[N:11]/[C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH:21]([CH3:23])[CH3:22])/[CH3:10])[C:3]=1[OH:24].[Li]CCCC.Br[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH3:38].O>C1COCC1.[Cl-].[Cl-].[Zn+2].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:21]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH:18]([CH3:20])[CH3:19])[C:12]=1/[N:11]=[C:9](/[C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])[C:3]=1[OH:24])\[CH3:10])([CH3:23])[CH3:22]

참가 물질

8

반응물 4

HCID 962WaterHCID 113582-BromoanisoleHCID 178418339ButyllithiumHCID 178463285HCID 178463285, 화합물

생성물 1

HCID 178489287HCID 178489287, 화합물수율 30%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 178418851HCID 178418851, 화합물촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-100 °C

실험 절차

To a solution of 1.94 g (5.0 mmol) of 30 in 20 mL of THF, 4.0 mL (10.0 mmol) of 2.5 M nBuLi in hexanes was added at −80° C. This mixture was stirred at this temperature for 1 hr, then cooled to −100° C., and 10.8 mL (10.8 mmol) of 1.0 M ZnCl2 in THF was added. The resulting mixture was slowly warmed to ambient temperature, stirred for 30 min, and then 2.82 g (15.0 mmol) of 2-bromoanisole and 0.14 g (0.25 mmol) of Pd(PtBu3)2 was added. This mixture was refluxed for 8 hr, then 5 mL of water was added. The resulting mixture was passed through short layer of silica gel 60. The silica gel layer was additionally washed with 30 mL of dichloromethane. The combined organic elute was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ether, 20:1, vol.) to give 0.62 g (30%) of yellowish solid.

후처리

  1. temperatureThe resulting mixture was slowly warmed to ambient temperature
  2. stirringstirred for 30 min
  3. temperatureThis mixture was refluxed for 8 hr
  4. washThe silica gel layer was additionally washed with 30 mL of dichloromethane
  5. washThe combined organic elute
  6. customwas evaporated to dryness
  7. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ether, 20:1, vol.)

출처 및 근거

ORD 기록
ord-43fab9aeb4764170bff78fec8f872540
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541521B2

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