Water → 1,4-Dimethoxy-3-methylnaphthalene-2-carbaldehyde

HRID 484024

반응식

HRID 484024 반응식
Br[C:2]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:15][CH3:16].CCCCCC.C([Li])CCC.CN(C)[CH:30]=[O:31].O>O1CCCC1>[CH:30]([C:2]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:15][CH3:16])=[O:31]

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 2922402-Bromo-1,4-dimethoxy-3-methylnaphthaleneHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 128475291,4-Dimethoxy-3-methylnaphthalene-2-carbaldehyde수율 48.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5.0 g (17.8 mmol) of 2-bromo-1,4-dimethoxy-3-methylnaphthalene in 30 ml of tetrahydrofuran was cooled to -78° C., to which 11.2 ml (17.9 mmol) of 1.6M n-butyllithium hexane solution was added dropwise, and stirred at the same temperature for 10 minutes after completion of the addition. Then 1.3 g (17.8 mmol) of dimethylformamide was added dropwise to the reaction mixture, and stirred at room temperature for 1 hour after completion of the addition. Water was added to the reaction mixture, from which the product was extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified with silica gel column chromatography (hexane-isopropyl ether (8:2), and crystallized from hexane-isopropyl ether, to give 2.0 g (48.9%) of 2-formyl-1,4-dimethoxy-3-methylnaphthalene. m.p. 95°-96° C.

후처리

  1. additionwas added dropwise
  2. additionafter completion of the addition
  3. stirringstirred at room temperature for 1 hour
  4. additionafter completion of the addition
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified with silica gel column chromatography (hexane-isopropyl ether (8:2)
  10. customcrystallized from hexane-isopropyl ether

출처 및 근거

ORD 기록
ord-78bfad3750a0479ca2aeea767dc20a24
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05229385

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