Bromine → HCID 14986492、化合物

HRID 257210ノート

反応式

HRID 257210 の反応式
[Br:1]Br.[OH:3][CH:4]1[C:9]([CH3:11])([CH3:10])[O:8][C:7]2[CH:12]=[CH:13][S:14][C:6]=2[CH:5]1[N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20]>ClCCl>[Br:1][C:13]1[S:14][C:6]2[CH:5]([N:15]3[CH2:19][CH2:18][CH2:17][C:16]3=[O:20])[CH:4]([OH:3])[C:9]([CH3:10])([CH3:11])[O:8][C:7]=2[CH:12]=1

参加物

4

反応物 2

HCID 24408BromineHCID 99034645,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyran

生成物 1

HCID 14986492HCID 14986492、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of bromine (0.20 mL, 3.92 mmol) in dichloromethane (5 mL) was slowly added to a solution of 5,6-dihydro-6-hydroxy-5,5-dimethyl-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyran (1.0 g, 3.74 mmol) at -5° C. The resultant mixture was stirred at rt for 2 h. The resulting precipitate was collected by filtration and purified by medium pressure chromatography using 5% methanol in dichloromethane as the eluant to give the product as a colorless solid, 0.28 g (22%): mp 162°-165° C.; IR(KBr): 3287, 1666 and 1570 cm-1 ; MS m/z: 346 (MH+); 1H NMR (CDCl3): δ1.30 (s, 3H), 1.47 (s, 3H), 2.06 (m, 2H), 7.50 (m, 2H), 3.23 (bs, 1H, exchanges with D2O), 3.34 (m, 2H), 3.76 (d, J=9.1 Hz, 1H) 5.16 (d, J=9.1 Hz, 1H) and 6.56 (s, 1H).

後処理

  1. filtrationThe resulting precipitate was collected by filtration
  2. custompurified by medium pressure chromatography

出典と根拠

ORDレコード
ord-152d1bf83325490690113bad92873f50
出典データセット
uspto-grants-1993_11
特許番号
US05260453

反応ノート

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