Tetrahydrofuran → (4-Chloro-2-methoxyphenyl)(pyridin-3-yl)methanol

HRID 272750

반응식

HRID 272750 반응식
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.C1COCC1.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[C:21]([O:27][CH3:28])[CH:20]=1>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[OH:24])=[C:21]([O:27][CH3:28])[CH:20]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 122863-BromopyridineHCID 138651154-Chloro-2-methoxybenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 69219148(4-Chloro-2-methoxyphenyl)(pyridin-3-yl)methanol수율 27%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
-60 °C

실험 절차

Toluene (3.5 mL) was added to a 3-necked flask and cooled to −60° C. n-BuLi (1.3 mL, 2.5M in hexanes) was added. A solution of 3-bromopyridine (0.3 mL, 3 mmol) in toluene (1.2 mL) was added dropwise to maintain internal temperature <−50° C. The resulting slurry was then stirred for 30 minutes at −60° C. THF (1.2 mL) was added dropwise, and the mixture was stirred for an additional 15 minutes. 4-Chloro-2-methoxy-benzaldehyde (561 mg, 3.3 mmol) was added and the mixture was allowed to warm to room temperature. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate to provide 201 mg (27%) of the title compound. MS (ESI) m/e 250 (M+H)+.

후처리

  1. additionwas added
  2. temperatureto maintain internal temperature <−50° C
  3. stirringthe mixture was stirred for an additional 15 minutes
  4. temperatureto warm to room temperature
  5. customThe reaction was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-c3f99ba394d54b32a60754169fba8c3c
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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