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Hydrochloric Acid → [3-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]methanol

HRID 1408403
ノート
印刷プレビュー

反応式

HRID 1408403 の反応式
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10](OC)=[O:11])[N:3]=1.C1COCC1.[Li+].[BH4-].Cl>O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[CH:14]=[CH:15][CH:16]=2)[N:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 53429639Methyl 3-(5-methyl-1,2,4-oxadiazol-3-YL)benzoate

生成物 1

HCID 7060550[3-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]methanol

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

3.46 g of methyl 3-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate (15.86 mmol) are dissolved in 50 ml of abs. THF in a 250 ml three-necked flask, and 0.691 g of LiBH4 (31.71 mmol) is subsequently introduced in portions with stirring at 0° C. under a nitrogen atmosphere, and the mixture is stirred without cooling for a further 20 h. For work-up, the reaction mixture is adjusted to pH 7 by slow dropwise addition of 1 N HCl with stirring, diluted with 100 ml of water and extracted 3× with 50 ml of dichloromethane. The combined organic phases are washed 1×100 ml of water, dried over sodium sulfate and evaporated to dryness in a rotary evaporator. The purification is carried out by chromatography (50 g of silica gel/DCM+0-1% of MeOH). The product is crystallised from diethyl ether/petroleum ether; m.p. 57-58° C.

後処理

  1. stirringthe mixture is stirred
  2. temperaturewithout cooling for a further 20 h
  3. stirringwith stirring
  4. extractionextracted 3× with 50 ml of dichloromethane
  5. washThe combined organic phases are washed 1×100 ml of water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness in a rotary evaporator
  8. customThe purification
  9. customThe product is crystallised from diethyl ether/petroleum ether

出典と根拠

ORDレコード
ord-4210e8287dbc4d74a496fbd19cb1a9ea
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921357B2

反応ノート

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