Triethylamine → 3-chloro-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one

HRID 552900ノート

反応式

HRID 552900 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]3[O:15][C:16](=[O:18])[CH:17]=[C:10]23)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:26]N1C(=O)CCC1=O>C(#N)C>[Cl:26][C:17]1[C:16](=[O:18])[O:15][CH:11]2[CH2:12][CH2:13][CH2:14][N:9]([CH2:8][C:5]3[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:10]=12

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31398Chlorosuccinimide2 回HCID 167527744-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one

生成物 1

HCID 577798103-chloro-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one収率 72.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

524 mg (1.98 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one (1-2) are dissolved in 20 ml of acetonitrile, then 414 μl (2.97 mmol) of triethylamine and 317 mg (2.37 mmol) of N-chlorosuccinimide are added at room temperature. After one hour of stirring, a 159 mg (1.19 mmol) of N-chlorosuccinimide are added. After a further hour of stirring, the entire reaction mixture is concentrated under reduced pressure. The residue is taken up in dichloromethane, washed successively twice with 1N aqueous hydrochloric acid, twice with 1N aqueous sodium hydroxide solution and saturated sodium chloride solution and dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (2:1) gives 430 mg (72% of theory) of 3-chloro-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one.

後処理

  1. stirringAfter a further hour of stirring
  2. customthe entire reaction mixture
  3. concentrationis concentrated under reduced pressure
  4. washwashed successively twice with 1N aqueous hydrochloric acid, twice with 1N aqueous sodium hydroxide solution and saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customConcentration of the organic phase under reduced pressure and purification of the residue column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

出典と根拠

ORDレコード
ord-03414f8302b240e0852f122954bcdfa3
出典データセット
uspto-grants-2011_05
特許番号
US07951951B2

反応ノート

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