3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one oxime → 3-(2,4-Dihydroxyphenyl)-2-cyclohexen-1-one Oxime

HRID 585691노트

반응식

HRID 585691 반응식
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[N:21][OH:22])[CH:16]=1>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[N:21][OH:22])[CH:16]=1

참가 물질

3

반응물 1

HCID 738836023-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one oxime

생성물 1

HCID 1363432473-(2,4-Dihydroxyphenyl)-2-cyclohexen-1-one Oxime수율 81.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one oxime (0.1 g) was heated to 50° C. in methanol (5 ml) containing acidic ion exchange resin (0.3 g). After 4 hr, the mixture was filtered and the resin was washed with ammonia solution (50 ml). Filtrate and washings were combined, evaporated in vacuo and purified by flash column chromatography (SiO2, ethyl acetate/petroleum ether, 3:2, v/v) to furnish the title compound as a yellow solid (0.058 g, 81%). δH (DMSO) (mixture of stereoisomers) 1.68 (2H, m, major), 1.76 (2H, m, minor), 2.26 (2H, m, minor), 2.40-2.54 (4H major+2H minor, overlapping m), 6.15-6.30 (3H major+2H minor, overlapping m), 6.85-6.95 (1H major+2H minor, overlapping m), 9.26 (1H, bs, major), 9.32 (1H, bs, minor), 9.35 (1H, bs, major), 9.40 (1H, bs, minor), 10.17 (1H, s, minor), 10.49(1H, s, major); m/z (ES−) 437 (2M−H)−.

후처리

  1. filtrationthe mixture was filtered
  2. washthe resin was washed with ammonia solution (50 ml)
  3. customevaporated in vacuo
  4. custompurified by flash column chromatography (SiO2, ethyl acetate/petroleum ether, 3:2, v/v)

출처 및 근거

ORD 기록
ord-6e38f62918fd4201a8b6dbbfa37fa37c
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933319B2

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