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

HRID 1532416노트

반응식

HRID 1532416 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0e78fb21530f41a2b50f3c1a6561bd49
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06201087B1

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