Water → 6-fluoro-3,4-dihydro-2-phenyl-1(2H)-naphthalenone

HRID 22196노트

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HRID 22196 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(C(OC)=O)[CH2:6][CH2:5]2.[Cl-].[Li+].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 57050899Methyl 6-fluoro-1,2,3,4-tetrahydro-1-oxo-2-phenyl-2-naphthalenecarboxylate

생성물 1

HCID 139534336-fluoro-3,4-dihydro-2-phenyl-1(2H)-naphthalenone수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

The tetralone from Step B (2.8 g, 9.4 mmole) was dissolved in 45 ml of dimethylformamide. To this solution was added lithium chloride (2.0 g, 47 mmole) and water (0.42 ml, 23 mmole). The reaction mixture was heated to 150° C. for 2.5 hrs and then cooled and partitioned between ether and water. The aqueous phase was separated and extracted three times with ether. The combined organic phases were washed once with water, dried (MgSO4), and concentrated (1.96 g, 87% yield). 1H NMR (CDCl3) δ: 8.13 (1H, dd, J=6,10 Hz), 7.31 (5H, m) 6.99 (2H, m), 3.80 (1H, m), 3.07 (2H, m), 2.43 (2H, m).

후처리

  1. temperaturecooled
  2. custompartitioned between ether and water
  3. customThe aqueous phase was separated
  4. extractionextracted three times with ether
  5. washThe combined organic phases were washed once with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated (1.96 g, 87% yield)

출처 및 근거

ORD 기록
ord-6ff7a09fc901415cac37fb3dec45b7b5
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428027

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