Diisopropylamine → 1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(3,5-dichloropyrid-4-yl)ethanol

HRID 1489738

반응식

HRID 1489738 반응식
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([Cl:21])[C:19]=1[CH3:20].[CH:22]1([O:27][C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH:31]=[O:32])[CH2:26][CH2:25][CH2:24][CH2:23]1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH:22]1([O:27][C:28]2[CH:29]=[C:30]([CH:31]([OH:32])[CH2:20][C:19]3[C:18]([Cl:21])=[CH:17][N:16]=[CH:15][C:14]=3[Cl:13])[CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH2:23][CH2:24][CH2:25][CH2:26]1

참가 물질

8

반응물 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 109538273,5-Dichloro-4-methylpyridineHCID 178418339Butyllithium

생성물 1

HCID 216976801-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(3,5-dichloropyrid-4-yl)ethanol수율 84.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

A stirred solution of diisopropylamine (9.75 mL) in dry tetrahydrofuran (200 mL) at -70° C. is treated dropwise with a solution of butyl lithium in hexane (27.2 mL; 2.5M) and the solution is stirred for 30 minutes. It is then treated with a solution of 3,5-dichloro-4-methylpyridine (10.25 g) in dry tetrahydrofuran (60 mL) during 30 minutes, while keeping the temperature below -75° C., and the solution is then stirred for a further 30 minutes. It is then treated with 3-cyclopentyloxy-4-methoxybenzaldehyde (13.92 g) in dry tetrahydrofuran (60 mL) during 15 minutes, and stirred for a further 1 hour 30 minutes at -75° C. The solution is treated with aqueous ammonium chloride solution and extracted with ethyl acetate (3×100 mL). The organic layers are combined, washed with brine, dried and concentrated to low volume. The resulting precipitate is filtered off, to give 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(3,5-dichloropyrid-4-yl)ethanol (20.5 g), m.p. 124°-125° C.

후처리

  1. customthe temperature below -75° C.
  2. stirringthe solution is then stirred for a further 30 minutes
  3. stirringstirred for a further 1 hour 30 minutes at -75° C
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated to low volume
  8. filtrationThe resulting precipitate is filtered off

출처 및 근거

ORD 기록
ord-85df0920b6e34058b7f70fed5a120bd3
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05679696

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