Triethylamine → 2-oxo-2H-1-benzopyran-7-yl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate

HRID 1532416ノート

反応式

HRID 1532416 の反応式
[CH3:1][C:2](=[CH2:22])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)=[O:4].S(Cl)(Cl)=O.O[C:28]1[CH:37]=[C:36]2[C:31]([CH:32]=[CH:33][C:34](=[O:38])[O:35]2)=[CH:30][CH:29]=1.C(N(CC)CC)C>CN(C=O)C.C1COCC1>[CH3:22][C:2](=[CH2:1])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:28]2[CH:29]=[CH:30][C:31]3[CH:32]=[CH:33][C:34](=[O:38])[O:35][C:36]=3[CH:37]=2)=[O:18])=[CH:20][CH:21]=1)=[O:4]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 37303444-{[6-(Methacryloyloxy)hexyl]oxy}benzenecarboxylic acidHCID 5281426Umbelliferone

生成物 1

HCID 212518122-oxo-2H-1-benzopyran-7-yl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate収率 59.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

8.5 g (0.028 mol) of 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoic acid were treated with 10 ml of thionyl chloride and 3 drops of DMF and boiled under reflux for 4 hours. The excess thionyl chloride was removed completely, firstly in a water-jet vacuum and subsequently in a high vacuum. The acid chloride remaining was taken up in 20 ml of THF and slowly added dropwise at 0° C. to a suspension of 4.09 g (0.025 mol) of 7-hydroxy-coumarin and 4.25 ml of triethylamine in 30 ml of THF. The batch was stirred at room temperature overnight, filtered and the filtrate was evaporated to dryness. The residue was purified by column chromatography and subsequently by recrystallization from ethanol. 6.71 g of 2-oxo-2H-1-benzopyran-7-yl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate were isolated as a white powder; m.p. 98-104.5° C.

後処理

  1. temperatureunder reflux for 4 hours
  2. customThe excess thionyl chloride was removed completely, firstly in a water-jet vacuum and subsequently in a high vacuum
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by column chromatography and subsequently by recrystallization from ethanol

出典と根拠

ORDレコード
ord-0e78fb21530f41a2b50f3c1a6561bd49
出典データセット
uspto-grants-2001_03
特許番号
US06201087B1

反応ノート

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