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1,10-Phenanthroline → ethyl 4-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yloxy)benzoate

HRID 1798443
ノート
印刷プレビュー

反応式

HRID 1798443 の反応式
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][C@H:14]1[C@H:19]([OH:20])[CH2:18][C@@H:17]2[CH2:21][C@H:15]1[C:16]2([CH3:23])[CH3:22].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu](I)I>[CH3:13][C@H:14]1[C@H:19]([O:20][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:18][C@@H:17]2[CH2:21][C@H:15]1[C:16]2([CH3:22])[CH3:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 10524983(-)-Isopinocampheol

生成物 1

HCID 67388677ethyl 4-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yloxy)benzoate

試薬・触媒・溶媒 2

HCID 83717
Copper iodide
触媒
HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

Ethyl 4-iodobenzoate (276 mg), (1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol (154 mg), 1,10-phenanthroline (36 mg), copper iodide (19 mg) and cesium carbonate (652 mg) were combined in toluene (0.5 mL). The reaction was heated to 120° C. over 36 hours. The reaction mixture was removed from heat, allowed to cool, diluted with ethyl acetate and poured into water. The organic layer was washed thoroughly with water and brine, dried over MgSO4, filtered and concentrated under vacuum. The crude material was purified by flash chromatography eluting with 95/5 hexanes/ether.

後処理

  1. customThe reaction mixture was removed
  2. temperaturefrom heat
  3. temperatureto cool
  4. additiondiluted with ethyl acetate
  5. additionpoured into water
  6. washThe organic layer was washed thoroughly with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe crude material was purified by flash chromatography
  11. washeluting with 95/5 hexanes/ether

出典と根拠

ORDレコード
ord-128c9fe2385b4fe09aab780e8c377f6d
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08343967B2

反応ノート

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