Benzaldehyde → (2-phenyl-4H-[1,3]dioxino[5,4-b]pyridin-6-yl)methanol

HRID 437392ノート

反応式

HRID 437392 の反応式
[OH:1][CH2:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5]([CH2:10][OH:11])[N:4]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(F)(F)F.CCOCC>>[OH:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:1][CH2:2][C:3]=2[N:4]=1

参加物

4

反応物 3

HCID 240BenzaldehydeHCID 8000Boron trifluoride etherateHCID 4173663-Hydroxypyridine-2,6-dimethanol

生成物 1

HCID 428642(2-phenyl-4H-[1,3]dioxino[5,4-b]pyridin-6-yl)methanol収率 77%

実験手順

To a stirred suspension of 31 g. (0.2 mole) of 2,6-bis-(hydroxymethyl)-3-hydroxypyridine (U.S. Pat. No. 3,700,681) in 101 ml. (1 mole) of benzaldehyde at 20°-25° C. is added dropwise over 45 min. 56.7 g. (0.4 mole) of borontrifluoride etherate. The mixture is allowed to stir at room temperature for 2 hrs., and the excess benzaldehyde removed under reduced pressure. The residue, after standing at room temperature, is added to 75 ml. of a 10M aqueous sodium hydroxide solution, and the product extracted into methylene dichloride. The organic phase is separated, concentrated in vacuo to 100 ml. and the methylene dichloride diluted with n-hexane. The crude product which crystallizes is filtered and dried, 37.4 g. (77% yield), m.p. 85°-89° C. Further purification is effected by recrystallization from acetone-n-hexane, 22.1 g., m.p. 114°-118° C.

後処理

  1. additionTo a stirred suspension of 31 g
  2. custom, and the excess benzaldehyde removed under reduced pressure
  3. customafter standing at room temperature
  4. additionis added to 75 ml
  5. extractionof a 10M aqueous sodium hydroxide solution, and the product extracted into methylene dichloride
  6. customThe organic phase is separated
  7. concentrationconcentrated in vacuo to 100 ml
  8. additionand the methylene dichloride diluted with n-hexane
  9. customThe crude product which crystallizes
  10. filtrationis filtered
  11. customdried
  12. customFurther purification
  13. customis effected by recrystallization from acetone-n-hexane, 22.1 g

出典と根拠

ORDレコード
ord-e7bb09834a5e4089ab6b0bdb72659232
出典データセット
uspto-grants-1977_06
特許番号
US04031108

反応ノート

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