Cyclohexene → HCID 59444173、化合物

HRID 1968998ノート

反応式

HRID 1968998 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 59444173HCID 59444173、化合物収率 76%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5ef897a59068459c8af485e400552c8a
出典データセット
uspto-grants-2013_04
特許番号
US08426443B2

反応ノート

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