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

HRID 1352882노트

반응식

HRID 1352882 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%].

후처리

  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%)

출처 및 근거

ORD 기록
ord-381acb06826c4e2f8dc3de2b22c4131c
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220784B2

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