Cyclohexene → HCID 59444173, 화합물

HRID 1968998노트

반응식

HRID 1968998 반응식
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([N+:14]([O-])=O)[CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.C1CCCCC=1>[Pd].C(O)C>[NH2:14][C:9]1[CH:8]=[C:7]([C:2]2([CH3:1])[O:3][CH2:4][CH2:5][O:6]2)[CH:12]=[CH:11][C:10]=1[OH:13]

참가 물질

5

반응물 2

HCID 8079CyclohexeneHCID 190269674-(2-Methyl-1,3-dioxolan-2-yl)-2-nitrophenol

생성물 1

HCID 59444173HCID 59444173, 화합물수율 76%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A stirred mixture of 4-(2-methyl-1,3-dioxolan-2-yl)-2-nitrophenol D129 (2.40 g, 10.66 mmol), cyclohexene (4.38 g, 53.3 mmol) and 10% palladium on carbon (0.227 g, 0.213 mmol) in ethanol (75 mL) was heated to reflux for 6 hr under argon. The mixture was cooled to rt and the catalyst was removed by filtration through celite. The filtrate was concentrated to dryness in vacuo and the reside dissolved in 10% MeOH in DCM (20 mL) and passed through a SCX-2 cartridge (25 g) which was then eluted with further 10% MeOH in DCM to wash through any unreacted starting material and then with 2M ammonia in MeOH. The basic eluate was concentrated under vacuum to give the title compound as a yellow-brown solid (1.58 g, 76%).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 6 hr under argon
  3. customthe catalyst was removed by filtration through celite
  4. concentrationThe filtrate was concentrated to dryness in vacuo
  5. dissolutionthe reside dissolved in 10% MeOH in DCM (20 mL)
  6. washwas then eluted with further 10% MeOH in DCM
  7. washto wash through
  8. concentrationThe basic eluate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-5ef897a59068459c8af485e400552c8a
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426443B2

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