Ammonium Hydroxide → Phenol, 3-(1-ethyl-1,2,5,6-tetrahydro-3-pyridinyl)-

HRID 851142ノート

反応式

HRID 851142 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][N:11]([CH2:15][CH3:16])[CH2:12][CH2:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.Cl.[NH+]1C=CC=CC=1.[OH-].[NH4+]>O>[CH2:15]([N:11]1[CH2:12][CH2:13][CH:14]=[C:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH2:10]1)[CH3:16]

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 205026301-Ethyl-5-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridineHCID 21584435Pyridinium hydrochloride

生成物 1

HCID 3068138Phenol, 3-(1-ethyl-1,2,5,6-tetrahydro-3-pyridinyl)-収率 81.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
200 °C

実験手順

A mixture of 5.2 g of the product of Step A and 10.4 g of pyridinium hydrochloride was heated at 200° C. for 21/2 hours and the mixture was cooled and diluted with water. Ammonium hydroxide was added to the mixture which was then extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture to obtain 3.95 g of 3-(1-ethyl-1,2,5,6-tetrahydropyridin-3-yl)-phenol. 3.85 g of the latter were dissolved in 40 ml of isopropanol and 2.4 g of oxalic acid were added thereto. The mixture was cooled and filtered and the product was washed with isopropanol and dried to obtain 3.57 g of 3-(1-ethyl-1,2,5,6-tetrahydropyridin-3-yl)-phenol oxalate melting at 240° C.

後処理

  1. temperaturethe mixture was cooled
  2. extractionwas then extracted with methylene chloride
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture

出典と根拠

ORDレコード
ord-3d63e03a188c48f89ad514959e2eff0a
出典データセット
uspto-grants-1983_05
特許番号
US04382942

反応ノート

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