Diethyl Ether → 1-(5-Benzyloxy-2-methoxyphenyl)-1-(6-methoxy-3-pyridyl)methanol

HRID 35284

反応式

HRID 35284 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.CCOCC.C([Li])CCC.[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([O:36][CH3:37])=[C:32]([CH:35]=1)[CH:33]=[O:34])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1.CCCCCC>[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([O:36][CH3:37])=[C:32]([CH:33]([C:2]2[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[OH:34])[CH:35]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 27348955-Bromo-2-methoxypyridineHCID 109666945-(Benzyloxy)-2-methoxybenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 143331211-(5-Benzyloxy-2-methoxyphenyl)-1-(6-methoxy-3-pyridyl)methanol収率 72.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

5-Bromo-2-methoxypyridine (15.87 g) was dissolved in dry tetrahydrofuran (50 ml) and the solution cooled with mechanical stirring under nitrogen to -100° (ether/liquid nitrogen). A solution of n-butyl lithium in hexane (53 ml of a 1.6M solution) was added dropwise, maintaining the temperature below -90°; a white precipitate appeared. After 5 minutes, 5-benzyloxy-2-methoxybenzaldehyde (17.04 g) in dry tetrahydrofuran (150 ml) was added dropwise, maintaining the temperature below -95°. After the addition was complete, the mixture was stirred to 5°. The dark solution was quenched with excess saturated ammonium chloride, the organic layer removed, the aqueous extracted with ethyl acetate, then the combined organics dried with anhydrous magnesium sulphate and evaporated. The residue crystallised from ether/petroleum spirit to give 1-(5-benzyloxy-2-methoxyphenyl)-1-(6-methoxy-3-pyridyl)methanol (17.83 g, 72%), m.p. 80°-82°.

後処理

  1. temperaturethe solution cooled
  2. temperaturemaintaining the temperature below -90°
  3. temperaturemaintaining the temperature below -95°
  4. additionAfter the addition
  5. customThe dark solution was quenched with excess saturated ammonium chloride
  6. customthe organic layer removed
  7. extractionthe aqueous extracted with ethyl acetate
  8. dry with materialthe combined organics dried with anhydrous magnesium sulphate
  9. customevaporated
  10. customThe residue crystallised from ether/petroleum spirit

出典と根拠

ORDレコード
ord-dd0c801af3d941b0a45af3676b40bc6f
出典データセット
uspto-grants-1988_08
特許番号
US04766121

関連ノート

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