4-Methylmorpholine → (4-(Pyridin-4-yl)phenyl)methanol

HRID 427554ノート

反応式

HRID 427554 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([O-])=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Na+].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.C(O)(=O)C.CO>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 23673507Sodium 4-(pyridin-4-yl)benzoate

生成物 1

HCID 2795556(4-(Pyridin-4-yl)phenyl)methanol収率 33.4%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of sodium 4-(4-pyridyl)benzoate (500 mg, 2.26 mmol), and N-methylmorpholine (0.250 mL, 2.26 mmol) in tetrahydrofuran (12 mL) was treated with ethyl chloroformate (0.216 mL, 2.26 mmol). After 0.25 h, the mixture was treated with sodium borohydride (256 mg, 6.79 mmol) followed by methanol (24 mL) dropwise. After 0.5 h, the mixture was treated with 10% aqueous acetic acid and concentrated in vacuo. The residue was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide. The aqueous layer was extracted twice with ethyl acetate and the combined extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo to yield 140 mg of the title compound which was used without further purification.

後処理

  1. waitAfter 0.5 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialthe combined extracts were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2e96532fc7104547806015fa0a73857e
出典データセット
uspto-grants-2001_11
特許番号
US06313122B1

反応ノート

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