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

HRID 2307153노트

반응식

HRID 2307153 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-1066a94040bb4009a8f29631dd9a202d
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828460B2

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