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Hydrochloric Acid → 2-Fluoro-3-hydroxy-6-[4-(4-octyloxyphenyl)phenyl]pyridine

HRID 1780555
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인쇄 미리보기

반응식

HRID 1780555 반응식
C([N-]C(C)C)(C)C.[Li+].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[N:11]=1.B(OC(C)C)(OC(C)C)[O:38]C(C)C.Cl.[Cl-].[Na+]>O1CCCC1.CCCCCC.C(C1C=CC=CC=1)C.O1CCCC1>[F:9][C:10]1[C:15]([OH:38])=[CH:14][CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[N:11]=1
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 190469542-Fluoro-6-[4-(4-octyloxyphenyl)phenyl]pyridine

생성물 1

HCID 190469362-Fluoro-3-hydroxy-6-[4-(4-octyloxyphenyl)phenyl]pyridine

시약·촉매·용매

2
HCID 8028Tetrahydrofuran용매2회HCID 86585711Tetrahydrofuran hexane ethylbenzene용매

실험 절차

7.95 ml (15.90 mmol) of a 2-molar lithium diisopropylamide solution in tetrahydrofuran/hexane/ethylbenzene are added dropwise at -78° C. to 5.00 g (13.25 mmol) of 2-fluoro-6-[4-(4-octyloxyphenyl)phenyl]pyridine (prepared as described in Example 6) in 1000 ml of tetrahydrofuran, and the mixture is stirred for 4 hours. 5.98 (31.80 mmol) of triisopropyl borate in 10 ml of tetrahydrofuran are then added dropwise at -78° C., and the reaction mixture is stirred overnight, during which it warms to room temperature. After addition of 20 ml of 10% hydrochloric acid and stirring at room temperature for 1 hour, sodium chloride solution is added, the mixture is extracted with ether, the ether phase is washed with sodium chloride, dried over sodium sulfate, filtered and concentrated. The residue is taken up in 200 ml of tetrahydrofuran, boiled with 40 ml of 17.5% hydrogen peroxide solution at 80° C. for 2 hours and then distributed between water and ether. The ether phase is washed with sodium sulfite solution and water, dried over sodium sulfate, filtered, evaporated to dryness, and the residue is chromatographed on silica gel using 8:2 toluene/THF, giving 1.7 g of 2-fluoro-3-hydroxy-6-[4-(4-octyloxyphenyl)phenyl]pyridine. ##STR25##

후처리

  1. stirringthe reaction mixture is stirred overnight, during which it
  2. customwarms to room temperature
  3. stirringstirring at room temperature for 1 hour
  4. extractionthe mixture is extracted with ether
  5. washthe ether phase is washed with sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. waitboiled with 40 ml of 17.5% hydrogen peroxide solution at 80° C. for 2 hours
  10. washThe ether phase is washed with sodium sulfite solution and water
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated to dryness
  14. customthe residue is chromatographed on silica gel using 8:2 toluene/THF

출처 및 근거

ORD 기록
ord-c2c64de448b34f02ac7d4b295885a8ea
출처 데이터셋
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05630962

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