Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylate → 1-cyclohexyl-1-hydroxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19528

반응식

HRID 19528 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[CH:24]1([Mg]Cl)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)([OH:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 23249734Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylateHCID 178478990HCID 178478990, 화합물

생성물 1

HCID 116397521-cyclohexyl-1-hydroxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester수율 30.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (78 mg, 0.253 mmol) obtained in Example 1 was dissolved in THF, and 18%-cyclohexylmagnesium chloride (0.7 mL, 0.506 mmol) was added thereto, followed by stirring for 5 hrs at 0° C. 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 30 mg of the titled compound (yield: 30%).

후처리

  1. washThe 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-7a10624842704a7abc2067372af0646d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745439B2

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