Hydrochloric Acid → 2-(cis-3-Methoxy-cyclohexyloxy)-3-nitro-pyridine

HRID 406041

反応式

HRID 406041 の反応式
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][O:12][C@H:13]1[CH2:18][CH2:17][C@H:16](O)[CH2:15][CH2:14]1.F[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1.Cl.C1C[O:34]CC1>>[CH3:11][O:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([O:34][C:21]2[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:14]1

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2 回HCID 2733832Lithium HexamethyldisilazideHCID 27628172-Fluoro-3-nitropyridineHCID 178496631HCID 178496631、化合物

生成物 1

HCID 673825062-(cis-3-Methoxy-cyclohexyloxy)-3-nitro-pyridine

実験手順

LiHMDS (1 M solution in THF; 40.0 ml) was added slowly to an ice/ethanol-cooled solution of cis/trans-4-methoxy-cyclohexanol (5.00 g) in THF (10 ml). Cooling was suspended after the addition was complete and the mixture was stirred for 15 minutes at room temperature. A solution of 2-fluoro-3-nitro-pyridine (5.10 g) in THF (10 ml) was added slowly while the temperature was maintained below 24° C. The reaction mixture was stirred for 2 h at room temperature, neutralized by addition of hydrochloric acid (1M), and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was submitted to column chromatography (silica gel, petrol ether/ethyl acetate 70:30 50:50) to give the cis-isomer (5.82 g) and the trans-isomer (1.60 g).

後処理

  1. temperatureCooling
  2. additionafter the addition
  3. temperaturewas maintained below 24° C
  4. stirringThe reaction mixture was stirred for 2 h at room temperature
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give the cis-isomer (5.82 g)

出典と根拠

ORDレコード
ord-c94aadac8c314992ae9f019e086540ae
出典データセット
uspto-grants-2014_06
特許番号
US08754079B2

関連ノート

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