Phenol → Methyl 4-[2'-methoxy-5'-nitro-4'-(phenoxymethyl)phenoxy]butanoate

HRID 533492ノート

反応式

HRID 533492 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][C:10]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:12]([O:27][CH3:28])[CH:11]=1>CO>[CH3:28][O:27][C:12]1[CH:11]=[C:10]([CH2:9][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

参加物

4

反応物 2

HCID 996PhenolHCID 21101447Methyl 4-[4'-(bromomethyl)-2'-methoxy-5'-nitrophenoxy]butanoate

生成物 1

HCID 21101446Methyl 4-[2'-methoxy-5'-nitro-4'-(phenoxymethyl)phenoxy]butanoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a suspension of phenol (130 mg, 138 mmol) and methyl 4-[4′-(bromomethyl)-2′-methoxy-5′-nitrophenoxy]butanoate (7) (500 mg, 138 mmol) in anhydrous methanol (5 cm3) was added KtOBu (186 mg, 166 mmol). The resulting green mixture was stirred at r.t. for 30 mins after which time a white precipitate had formed. The precipitate was filtered and recrystallised from methanol affording the desired compound 9 as a pure white solid (319 mg, 61%). m.p. 96-98° C. Found C, 61.0; H, 5.8; N, 4.0; C19H21NO7 requires C, 60.8; H, 5.6; N, 3.7%; Rf 0.64 (SiO2, hexane:EtOAc 2:1 v/v); νmax (KBr disc)/cm−1 3000-2800 (m), 1720 (s), 1610, 1580, 1520, 1280, 1220; δH (300 MHz, CDCl3) 2.21 (2H, q, J=6.7 Hz, CH2), 2.57 (2H, t, J=6.7 Hz, CH2), 3.71 (3H, s, OCH3), 3.91 (3H, s, OCH3), 4.14 (2H, t, J=6.7 Hz, CH2), 5.50 (2H, s, CH2), 6.98-7.02 (3H, m, ar), 7.29-7.34 (3H, m, ar), 7.77 (1H, s, ar) ppm; δC (100 MHz, CDCl3) 24.7 (CH2), 30.4 (CH2), 51.7 (OCH3), 56.3 (OCH3), 67.0 (CH2), 68.2 (CH2), 109.4 (CH), 109.6 (CH), 115.0 (CH), 121.5 (CH), 129.6 (CH), 129.7 (CH), 138.9, 147.0, 154.3, 158.1, 173.2 (COOCH3) ppm; m/z (FAB) 376 [(MH), 20%], 282 [(M-C6H5O), 80%].

後処理

  1. additionwas added KtOBu (186 mg, 166 mmol)
  2. customhad formed
  3. filtrationThe precipitate was filtered
  4. customrecrystallised from methanol affording the desired compound 9 as a pure white solid (319 mg, 61%)

出典と根拠

ORDレコード
ord-3b6fca4ed7794a7d874e9c96bfc12c39
出典データセット
uspto-grants-2014_10
特許番号
US08853270B2

反応ノート

読み込み中…