Dicyclohexylcarbodiimide → HCID 86698886、化合物

HRID 76236ノート

反応式

HRID 76236 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]([OH:20])=[O:19])[CH2:17][CH2:16]3)=[CH:11][C:10]=2[F:21])[CH:5]=[CH:6][C:7]=1[Cl:8].C1(N=C=NC2CCCCC2)CCCCC1.[O:37]1[CH2:39][CH:38]1[CH2:40]O>C(Cl)Cl>[O:37]1[CH2:39][CH:38]1[CH2:40][O:19][C:18]([C:15]1([C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[C:10]([F:21])[CH:11]=2)[CH2:17][CH2:16]1)=[O:20]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 11164GlycidolHCID 9996409Chf-5074

生成物 1

HCID 86698886HCID 86698886、化合物収率 42.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-(3′,4′-Dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarboxylic acid (2.00 g, 6.15 mmol), dicyclohexylcarbodiimide (DCC, 2.54 g, 12.30 mmol), 4-dimethyl-aminopyridine (DMAP, 0.075 g, 0.614 mmol), and oxiran-2-ylmethanol (0.490 ml, 7.38 mmol) were dissolved in dry DCM (40 mL). The reaction mixture was stirred at room temperature (r.t.) overnight, then it was filtered and the filtrate was evaporated to dryness to afford 4.4 g of crude. The crude was purified by gradient flash chromatography eluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v) to afford 1-(3′,4′-dichloro-2-fluorobiphenyl-4-yl)cyclopropane carboxylic acid oxiranylmethyl ester (1.0 g, 42.6% yield).

後処理

  1. filtrationit was filtered
  2. customthe filtrate was evaporated to dryness
  3. customto afford 4.4 g of crude
  4. customThe crude was purified by gradient flash chromatography
  5. washeluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v)

出典と根拠

ORDレコード
ord-adf76516f8b940948a53a132b73a1d44
出典データセット
uspto-grants-2014_09
特許番号
US08835494B2

反応ノート

読み込み中…