Phosphoric Acid → HCID 15279438、化合物

HRID 865919ノート

反応式

HRID 865919 の反応式
[CH3:1][C:2](=[CH2:5])[C:3]#[CH:4].C(N(CC)CC)C.[CH3:13][C:14]1([CH3:33])[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:23](OS(C(F)(F)F)(=O)=O)[C:17]=2[C:16](=[O:32])[O:15]1.P(=O)(O)(O)O>CN(C)C=O.O>[CH3:13][C:14]1([CH3:33])[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:23]([C:4]#[C:3][C:2]([CH3:5])=[CH2:1])[C:17]=2[C:16](=[O:32])[O:15]1

参加物

7

反応物 4

HCID 1004Phosphoric AcidHCID 8471TriethylamineHCID 62323Isopropenylacetylene2 回HCID 10892748HCID 10892748、化合物

生成物 1

HCID 15279438HCID 15279438、化合物収率 62.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
115 °C

実験手順

0.64 g (0.92 mmol) of bistriphenylphosphinepalladium dichloride, 4.4ml (46 mmol) of 3-methyl-3-buten-1-yne and 24ml of triethylamine are added under nitrogen to a solution of 15.0 g (46 mmol) of 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H(1,3)benzodioxin-4-one in 150 ml of dimethylformamide. The mixture is heated at 115° C. for 0.5 h, a further 6.6 ml of 3-methyl-3-buten-1-yne are then added at this temperature in the course of 1 h and the reaction solution is subsequently stirred for 15 min. After cooling, it is poured into 500 ml of water containing phosphoric acid (pH 3) at 0° C. and extracted with methyl tert-butyl ether, and the combined organic phases are carefully washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated. 14 g of a dark oil remain, which is chromatographed on silica gel using n-hexane/ethyl acetate. 7.0 g of colorless crystals are obtained, m.p. 60° C. (cf. Table 1, No. 1.009).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with methyl tert-butyl ether
  3. washthe combined organic phases are carefully washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customwhich is chromatographed on silica gel

出典と根拠

ORDレコード
ord-5d1b5699aeca499093c96cd7009b46b5
出典データセット
uspto-grants-1996_10
特許番号
US05569640

反応ノート

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