Triethylamine → HCID 178418448、化合物

HRID 1724

反応式

HRID 1724 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:20])=[CH:14][C:15](=[O:19])[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C1(C)C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1>C1COCC1>[N+:37](=[C:14]1[C:13](=[O:20])[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[O:16][C:15]1=[O:19])=[N-:38]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 547084427-(Benzyloxy)-4-hydroxy-2H-1-benzopyran-2-one

生成物 1

HCID 178418448HCID 178418448、化合物収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of7-benzyloxy-4-hydroxy coumarin (2.5 g, 9.3 mmol; prepared in accordance with Example 5) in anhydrous THF (40 mL) was mixed with triethylamine (0.9 g, 9 mmol) taken in a 100 mL 3-neck round-bottom flask under an atmosphere of N2. A solution of p-toluenesulfonyl azide (2.8 g, 14 mmol) in dry THF (20 mL) was added dropwise through an addition funnel. The mixture was stirred at room temperature for 3 hrs. The color of the solution turned orange. The solvent was rotary evaporated and the product was taken in CH2Cl2 and washed with water (3 times). Petroleum ether (twice the volume) was added to the solution and the solid precipitate was filtered with a frit and dried at 45° C. The product was recrystallized using CH2Cl2 ; yield 90%. The product was characterized by NMR: 13C NMR (100 MHz, CD2 Cl2): 173.3, 165.4, 158.7, 156.0, 136.0, 129.1, 128.8, 128.0, 127.6, 113.9, 113.0, 103.0, 75.7, 71.2; DSC - m. pt. 191° C. followed by decomposition; IR (KBr): 2182, 2154, 1717, 1647, 1605 cm-1 ; MS(APCI): (M+H), 295 (base peak).

後処理

  1. customtaken in a 100 mL 3-neck round-bottom flask under an atmosphere of N2
  2. customThe solvent was rotary evaporated
  3. washwashed with water (3 times)
  4. additionPetroleum ether (twice the volume) was added to the solution
  5. filtrationthe solid precipitate was filtered with a frit
  6. customdried at 45° C
  7. customThe product was recrystallized

出典と根拠

ORDレコード
ord-2be13a8581c44d4eb5c7cef82a7c8e6c
出典データセット
uspto-grants-1998_03
特許番号
US05726296

関連ノート

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