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

HRID 862085노트

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HRID 862085 반응식
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

참가 물질

5

반응물 3

HCID 10036812HCID 10036812, 화합물HCID 19701585Methoxymethyl 2-methoxymethoxy-5-methylbenzoateHCID 178418244HCID 178418244, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-88e5e0125cad43eebe318c5630f29be9
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716971

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