Methanol → [2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

HRID 1404521노트

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HRID 1404521 반응식
[CH:1]1([C:4]2[C:13]([CH:14]=[O:15])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.CO.O1CCCC1.[BH4-].[Na+]>CCCCCC.C(OCC)(=O)C.O>[CH:1]1([C:4]2[C:13]([CH2:14][OH:15])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:2][CH2:3]1

참가 물질

8

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 99479742-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde

생성물 1

HCID 9817555[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol수율 96%

시약·촉매·용매 3

HCID 962Water용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

2-Cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde (30 gm) was added methanol (30 ml) and tetrahydrofuran (270 ml) at room temperature. The reaction mixture was then cooled to 0° C. and then added sodium borohydride (5.8 gm) for 30 minutes at 0 to 5° C. The reaction mass was stirred for 1 hour 30 minutes and then added water (150 ml) and ethyl acetate (150 ml). The reaction mass was stirred for 10 minutes, and then the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate and then concentrated to obtain a residual solid. To the residual solid was added n-hexane (150 ml) and stirred for 30 minutes. The separated solid was filtered and dried to obtain 29 gm of (2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol.

후처리

  1. stirringThe reaction mass was stirred for 10 minutes
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. concentrationconcentrated
  6. customto obtain a residual solid
  7. stirringstirred for 30 minutes
  8. filtrationThe separated solid was filtered
  9. customdried

출처 및 근거

ORD 기록
ord-94e83b968ed24290875080b6c8fbe10d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912333B2

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