Salicylaldehyde → 6a,11a-Dihydro-9-methoxy-6-H-[1]benzothieno[3,2-c][1]benzopyran-6-one

HRID 1712

反応式

HRID 1712 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[CH2:7][C:8]([S:10][C:5]=2[CH:4]=1)=[O:9].[CH:13](=O)[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[OH:16]>C(O)C.C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[CH:7]3[CH:13]([S:10][C:5]=2[CH:4]=1)[C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[O:16][C:8]3=[O:9]

参加物

6

反応物 2

HCID 6998SalicylaldehydeHCID 154582606-Methoxythianaphthen-2-one

生成物 1

HCID 852145536a,11a-Dihydro-9-methoxy-6-H-[1]benzothieno[3,2-c][1]benzopyran-6-one収率 83%

試薬・触媒・溶媒 3

HCID 8471Triethylamine触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 6-methoxythianaphthen-2-one (52.6 g, 290 mmol) in a mixture of ethanol (260 mL) and methylene chloride (130 mL) was added triethylamine (2.0 mL, 14.8 mmol) followed by salicylaldehyde (32 mL, 300 mmol) at room temperature. After 1 h, a solid began to precipitate and stirring was continued for 3.5 h. The mixture was then diluted with cold hexane and filtered to yield 68.3 g (83%) of the title product as a powdery white solid, pure by 1H-NMR analysis: 1H NMR (300 MHz, CDCl3) δ7.45 (d, J=7.5 Hz, 1H), 7.33 (m, 2H), 7.17 (m, 1H), 7.07 (d, J=8.1 Hz, 1H), 6.77 (d, J=2.4 Hz, 1H), 6.69 (dd, J=2.4, 8.5 Hz, 1H), 5.25 (d, J=7.4 Hz, 1H), 4.37 (d, J=7.3 Hz, 1H), 3.77 (s, 3H); 13C NMR (75 MHz, CDCl3) δ166.4, 160.7, 150.8, 141.4, 130.1, 129.0, 127.7, 127.0, 124.9, 119.5, 117.2, 111.2, 108.3, 55.5, 50.6, 49.6; IR (CHCl3) 1766 cm-1 ; MS (FD) m/e 284 (M+); Anal. calc'd. for C16H12O3S: C, 67.59; H, 4.26. Found: C, 67.77; H, 4.24.

後処理

  1. customto precipitate
  2. waitwas continued for 3.5 h
  3. additionThe mixture was then diluted with cold hexane
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-5ac5c62883484e62b790bfad4bc5e3bb
出典データセット
uspto-grants-1998_03
特許番号
US05726186

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