Hydrochloric Acid → HCID 59637336、化合物

HRID 1842861ノート

反応式

HRID 1842861 の反応式
Cl[CH:2]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].Cl>CN(C=O)C.O>[CH:8]1([CH:2]([C:19]2[CH:18]=[CH:17][C:16]([N+:21]([O-:23])=[O:22])=[C:15]([F:14])[CH:20]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 738951-Fluoro-2-nitrobenzeneHCID 13215910HCID 13215910、化合物

生成物 1

HCID 59637336HCID 59637336、化合物収率 49%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
-45 °C

実験手順

8.2 g of potassium tert.butylate were dissolved in 70 ml of DMF and cooled to −45° C. For this purpose, a mix of ethyl 2-chloro-2-cyclohexylacetate (36.6 mmol, 7.5 g) and 1-fluoro-2-nitrobenzene (36.6 mmol, 3.9 ml) was carefully added dropwise and stirred for a further 20 minutes. The reaction mix was set to pH 4 using 16% HCl, diluted with 25 ml of water and extracted with EtOAc (3×50 ml). Once combined, the organic phases were washed with water and sat. aq. NaCl sol., dried over MgSO4 and concentrated under vacuum. The resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EtOAc in cyclohexane) and produced 5.5 g (49%) of product.

後処理

  1. additionwas carefully added dropwise
  2. additionThe reaction mix
  3. extractionextracted with EtOAc (3×50 ml)
  4. washthe organic phases were washed with water and sat. aq. NaCl sol.
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-38817994863b4e16b0c3ffa8aab63b5d
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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