Formaldehyde → 1-[(6-hydroxy-2,2-dimethyl-4-oxo-4H-1,3-dioxin-5-yl)methyl]pyridinium hydroxide

HRID 5134

反応式

HRID 5134 の反応式
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH2:11]=O.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[OH-:3].[OH:8][C:7]1[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4](=[O:5])[C:6]=1[CH2:11][N+:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

4

反応物 3

HCID 712FormaldehydeHCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

生成物 1

HCID 197978551-[(6-hydroxy-2,2-dimethyl-4-oxo-4H-1,3-dioxin-5-yl)methyl]pyridinium hydroxide収率 91.6%

実験手順

Meldrum's acid (20 g, 0.139 mol) was dissolved in 50 ml of pyridine. The solution immediately turned yellow and was somewhat exothermic. After dissolution was complete, a 37% aqueous solution of formaldehyde (10.4 ml, 0.139 mol) was added in one portion. The reaction mixture was allowed to stir for one hour under argon. The solvent was removed in vacuo at 55° C. after which yellow crystals were isolated. These crystals were then stirred with 200 ml of hexanes for 30 minutes and filtered providing 32.24 g (0.127 mol, 91.6%) of the desired title product. Melting point: >350° C. NMR (ppm): 1.62 (s, 6H (CH3)); 5.58 (bs, 2H (CH2)); 7.71 (t, 2H (Ar-H)); 8.17 (t, 1H (Ar-H)); 9.0 (d, 2H (Ar-H)). MS: 235.23.

後処理

  1. dissolutionAfter dissolution
  2. customThe solvent was removed in vacuo at 55° C. after which yellow crystals
  3. customwere isolated
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-bff13585dd6045868860fbe58d6d87e2
出典データセット
uspto-grants-1993_09
特許番号
US05243053

関連ノート

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