Tetrahydrofuran → 1-hydroxy-6-methoxy-1,3-diphenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19523

반응식

HRID 19523 반응식
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](OC)[CH:16]=1)[C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[C:24]1([Mg]Cl)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1C[O:35][CH2:34]C1>>[CH2:1]([O:3][C:4]([C:5]1[C:6]([OH:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:24]2[C:29]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:28][CH:27]=[C:26]([O:35][CH3:34])[CH:25]=2)=[O:23])[CH3:2]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 118449532-(3-Methoxy-benzyl)-3-oxo-3-phenyl-propionic acid ethyl esterHCID 178478979HCID 178478979, 화합물

생성물 1

HCID 115961681-hydroxy-6-methoxy-1,3-diphenyl-1H-indene-2-carboxylic acid ethyl ester수율 76%

반응 조건

온도
0 °C

실험 절차

The compound (300 mg, 0.97 mmol) obtained in Step 1 was dissolved in THF and 1.5 equivalents of phenylmagnesium chloride were added thereto, followed by stirring for 1 hr at 0° C. Then, the resulting mixture washed with saturated saline, and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 285 mg of the titled compound (yield: 76%).

후처리

  1. washThen, the resulting mixture washed with saturated saline
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-6752d39a677c4ee1b9821a25bdb58aaf
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745439B2

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