4-Methylmorpholine → [4-(Morpholin-4-yl)phenyl]methanol

HRID 1837157ノート

反応式

HRID 1837157 の反応式
[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O.CO>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:14][CH:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

参加物

8

反応物 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 3452784-(Morpholin-4-yl)benzoic acidHCID 4311764Sodium borohydride

生成物 1

HCID 2776456[4-(Morpholin-4-yl)phenyl]methanol収率 18%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-(4-morpholinyl)benzoic acid (1.00 g, 4.83 mmol) and 4-methylmorpholine (0.53 mL, 4.8 mmol) in tetrahydrofuran (25 mL) at −10° C. was treated with ethyl chloroformate (0.46 mL, 4.8 mmol). After 0.25 h, the mixture was treated with sodium borohydride (550 mg, 14.5 mmol) followed by MeOH (50 mL) slowly. The mixture was then treated with 5% HOAC in water and the mixture was concentrated. The residue was purified by chromatography (SiO2, EtOAc:hexanes) yielding 164 mg (18%) of the title compound.

後処理

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by chromatography (SiO2, EtOAc:hexanes)

出典と根拠

ORDレコード
ord-728689b4e2a94e7cbdbb0df13e37bd3a
出典データセット
uspto-grants-2004_08
特許番号
US06780878B2

反応ノート

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