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

HRID 272750

反応式

HRID 272750 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-60 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c3f99ba394d54b32a60754169fba8c3c
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

関連ノート

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