Nitric Acid → HCID 178500687、化合物

HRID 1713795ノート

反応式

HRID 1713795 の反応式
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[C:10]1([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:13]1[CH:14]=[CH:15][C:10]([C@H:16]2[CH2:17][CH2:18][C@H:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:20][CH2:21]2)=[CH:11][CH:12]=1)([O-:4])=[O:2]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 178500650HCID 178500650、化合物

生成物 1

HCID 178500687HCID 178500687、化合物

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 65% nitric acid (3.95 mL) and 95% sulphuric acid (4.97 mL) was added dropwise to a stirred solution of methyl (trans-4-phenylcyclohexyl)acetate (4710 mg) in CCl4 (20 mL) at 5° C. and the solution was allowed to warm to ambient temperature and stirred for 16 hours. Ice/water (50 mL) was added and the mixture was extracted with DCM (2×40 mL). The organic extracts were combined, washed with brine (50 mL), dried, and concentrated in vacuo to give an oil. This oil was purified by flash chromatography on a 80 g Biotage™ silica column, using a gradient of 0-20% EtOAc in hexane as the eluent to give crude methyl [trans-4-(4-nitrophenyl)cyclohexyl]acetate which was dissolved in ethyl acetate (30 mL). 10% palladium on carbon (0.400 g) was added and the resulting suspension was stirred at ambient temperature for 16 hours under an atmosphere of hydrogen. The suspension was filtered through diatomaceous earth and concentrated in vacuo to give a solid. This was purified by flash chromatography on a 40 g Biotage™ silica column using a gradient of 20-45% EtOAc/hexane as eluent to give the title compound (1740 mg) as a solid; 1H NMR δ 6.83 (2H, d), 6.46 (2H, d), 4.72 (2H, s), 3.59 (3H, s), 2.23 (3H, m), 1.72 (5H, m), 1.35 (2H, m), 1.09 (2H, m); MS m/e MH+ 248.

後処理

  1. extractionthe mixture was extracted with DCM (2×40 mL)
  2. washwashed with brine (50 mL)
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThis oil was purified by flash chromatography on a 80 g Biotage™ silica column

出典と根拠

ORDレコード
ord-712757450d6f43eaa38796fef10fb0c2
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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