HCID 10036812、化合物 → 3-(1,3-Dioxolan-2-yl)-2-(2-methoxymethoxy-5-methylbenzoyl)pyridine

HRID 862085ノート

反応式

HRID 862085 の反応式
Br[C:2]1[C:7]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.[CH3:24][O:25][CH2:26][O:27][C:28]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][C:29]=1[C:30](OCOC)=[O:31]>C1COCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:7]1[C:2]([C:30](=[O:31])[C:29]2[CH:36]=[C:37]([CH3:40])[CH:38]=[CH:39][C:28]=2[O:27][CH2:26][O:25][CH3:24])=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 10036812HCID 10036812、化合物HCID 19701585Methoxymethyl 2-methoxymethoxy-5-methylbenzoateHCID 178418244HCID 178418244、化合物

生成物 1

HCID 197015733-(1,3-Dioxolan-2-yl)-2-(2-methoxymethoxy-5-methylbenzoyl)pyridine収率 41.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-bromo-3-(1,3-dioxolan-2-yl)pyridine (3.50 g) in THF (50 ml) was added, at -78° C. under argon atmosphere, a 1.6M n-butyl lithium hexane solution (10.5 ml), which was stirred for 20 minutes. This reaction mixture was added, at the same temperature under argon atmosphere, to a solution of methoxymethyl 2-methoxymethoxy-5-methylbenzoate (3.66 g) in THF (50 ml). The mixture was stirred for 40 minutes, then for further one hour while warming up to room temperature. The reaction mixture was poured into a saturated aqueous saline solution, followed by extraction with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate) and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give 3-(1,3-dioxolan-2-yl)-2-(2-methoxymethoxy-5-methylbenzoyl)pyridine (2.06 g) (Compound E-14). The physical properties and spectrum data are shown in Table 16 and Table 19.

後処理

  1. additionThe reaction mixture was poured into a saturated aqueous saline solution
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract solution was washed with a saturated aqueous saline solution
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-88e5e0125cad43eebe318c5630f29be9
出典データセット
uspto-grants-1998_02
特許番号
US05716971

反応ノート

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