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

HRID 1780555
ノート
印刷プレビュー

反応式

HRID 1780555 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 86585711Tetrahydrofuran hexane ethylbenzene溶媒

実験手順

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##

後処理

  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

出典と根拠

ORDレコード
ord-c2c64de448b34f02ac7d4b295885a8ea
出典データセット
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05630962

反応ノート

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