Formaldehyde → 3,4-Dihydro-6-methoxy-2-methylene-1(2h)-naphthalenone

HRID 432594노트

반응식

HRID 432594 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.C=O.F[C:17](F)(F)C([O-])=O.C[NH2+]C1C=CC=CC=1.CCOCC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8](=[CH2:17])[CH2:7][CH2:6]2

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 141126-Methoxy-alpha-tetraloneHCID 2724109N-Methylanilinium trifluoroacetate

생성물 1

HCID 113444693,4-Dihydro-6-methoxy-2-methylene-1(2h)-naphthalenone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 6-methoxytetralone (29.24 g, 165.9 mmol), paraformaldehyde (22.4 g, 746.6 mmol) and N-methylanilinium trifluoroactate (55 g, 248.9 mmol) in 250 mL THF was refluxed for 4 hours and allowed to come to room temperature. To this was added ether (250 mL) with stirring and the mixture was decanted to remove the gummy precipitate. The supernatant was washed with sat. NaHCO3, the oganic layer was dried (MgSO4) and concentrated. The residue was redissolved in ether, filtered through celite and concentrated to afford the title compound as a thick yellow oil.

후처리

  1. temperaturewas refluxed for 4 hours
  2. customto come to room temperature
  3. customthe mixture was decanted
  4. customto remove the gummy precipitate
  5. washThe supernatant was washed with sat. NaHCO3
  6. dry with materialthe oganic layer was dried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe residue was redissolved in ether
  9. filtrationfiltered through celite
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c7eb14bfbdd84499bd6a79efe0b6eb5b
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664250B2

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