Hydrochloric Acid → 2-Phenyl-3-pyridinol

HRID 481745

反応式

HRID 481745 の反応式
Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>C1(C)C=CC=CC=1.C(O)C.[OH-].[Na+].O>[OH:8][C:7]1[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 3

HCID 313Hydrochloric AcidHCID 230702-Bromo-3-pyridinolHCID 66827Phenylboronic Acid

生成物 1

HCID 187052-Phenyl-3-pyridinol収率 45.4%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-bromo-3-hydroxypyridine (2.20 g, 12.6 mmol), phenylboronic acid (2.00 g, 16.3 mmol) and palladium (tetrakis)triphenylphosphine (250 mg) in toluene (30 mL), ethanol (15 mL) and 5% aqueous sodium hydroxide (15 mL) was degassed with a stream of nitrogen and stirred vigorously at 100° C. overnight. The mixture was diluted with water (50 mL) and ethyl acetate (100 mL), and the organic layer was dried over sodium sulfate and concentrated, affording a yellow solid. This material was suspended in water (100 mL), a few mL of 1N HCl was added, and the resulting solution was extracted with ethyl acetate. The aqeuous layer was neutralized with saturated aqueous sodium bicarbonate, and again was extracted with ethyl acetate. The combined organic extracts were dried with sodium sulfate and concentrated to an oily solid, which was triturated with 2:1 hexane/ethylacetate, affording 0.98 g of 3-hydroxy-2-phenylpyridine.

後処理

  1. customwas degassed with a stream of nitrogen
  2. additionThe mixture was diluted with water (50 mL) and ethyl acetate (100 mL)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customaffording a yellow solid
  6. extractionthe resulting solution was extracted with ethyl acetate
  7. extractionagain was extracted with ethyl acetate
  8. dry with materialThe combined organic extracts were dried with sodium sulfate
  9. concentrationconcentrated to an oily solid, which
  10. customwas triturated with 2:1 hexane/ethylacetate

出典と根拠

ORDレコード
ord-8a5361bd9518460199bb79193a1b9d7c
出典データセット
uspto-grants-1998_08
特許番号
US05789584

関連ノート

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