Diethyl Ether → 4-(2-Phenyl-chroman-6-yloxy)-1-propyl-cyclohexanol

HRID 59778

반응식

HRID 59778 반응식
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH:18]4[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25]([Mg]Cl)[CH2:26][CH3:27].C(OCC)C.[Cl-].[NH4+]>O1CCCC1>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH:18]4[CH2:23][CH2:22][C:21]([CH2:25][CH2:26][CH3:27])([OH:24])[CH2:20][CH2:19]4)[CH:13]=3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 903901554-(2-Phenyl-chroman-6-yloxy)-cyclohexanoneHCID 178455855HCID 178455855, 화합물

생성물 1

HCID 903900044-(2-Phenyl-chroman-6-yloxy)-1-propyl-cyclohexanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

100 mg of 4-(2-phenyl-chroman-6-yloxy)-cyclohexanone were dissolved at room temperature in 5 ml of tetrahydrofuran. A 2M solution of propylmagnesium chloride in diethyl ether (0.31 ml, 2 eq) was added, and stirring at room temperature was continued for 4 h. The reaction was stopped by careful addition of saturated aqueous ammonium chloride solution. The aqueous layer was extracted with methyl tert-butyl ether. The organic layer was dried over sodium sulfate and filtered, and the solvent removed by evaporation. The resulting oil was chromatographed over silica gel using heptane/ethyl acetate 20:1 as the eluent. 54 mg of the title compound were isolated as a pale yellow oil (48%).

후처리

  1. extractionThe aqueous layer was extracted with methyl tert-butyl ether
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation
  5. customThe resulting oil was chromatographed over silica gel

출처 및 근거

ORD 기록
ord-81069c4c704e42ddb46130f780f09869
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440941B2

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