Hydrochloric Acid → 5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone

HRID 1463248

反応式

HRID 1463248 の反応式
[CH2:1]([C:3]1[C:4](=[O:25])[N:5]([CH2:22][C:23]#[CH:24])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]3OCC[O:18]3)[CH:12]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2].Cl.CCOCC.O>C(OCC)(=O)C.CCCCCC>[CH2:1]([C:3]1[C:4](=[O:25])[N:5]([CH2:22][C:23]#[CH:24])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 218084975,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone

生成物 1

HCID 196906845,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone収率 86.4%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of 2.3 g (6.8 mmol) of 5,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone in 1 mL of ethyl acetate was added 50 mL of 6M hydrochloric acid and the mixture was stirred for 4 hours. The reaction was followed by gas chromatography and TLC(20% ethyl acetate in hexane). Upon completion of reaction, 75 mL of ether and 150 mL of water were added to the reaction mixture. The layers were separated and the aqueous layer was extracted twice with 50 mL of ether. The organic layers were combined, dried over MgSO4 and concentrated to yield 1.73 g of 5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone (Compound 69) as a yellow oil (86%), which solidified on standing. Mp.=82°-86° C. 1H-NMR (CDCl3) δ1.25(6H,m), 2.4(1H,t), 2.65(4H,q), 4.6(2H,d), 7.7(1H,t), 8.05(2H,m), 8.25(1H,s), 10.15(1H,s).

後処理

  1. additionwere added to the reaction mixture
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with 50 mL of ether
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-05e89660e98c45938ddcf136e316991d
出典データセット
uspto-grants-1994_04
特許番号
US05300477

関連ノート

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