1,3-Propanediol → HCID 58729335、化合物

HRID 552875ノート

反応式

HRID 552875 の反応式
[C:1]1(B(O)O)[C:9]([CH3:10])=[C:7]([CH3:8])[CH:6]=[C:4]([CH3:5])[C:2]=1[CH3:3].[CH2:14](O)[CH2:15][CH2:16]O.Br[C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][C:26](Br)=[CH:27][CH:28]=3)[C:23]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:22]=2[CH:21]=1.C([O-])([O-])=O.[K+].[K+]>O.C1(C)C=CC=CC=1>[CH3:3][C:2]1[C:4]([CH3:5])=[CH:6][C:7]([CH3:8])=[C:9]([CH3:10])[C:1]=1[C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][C:26]([C:14]4[C:4]([CH3:5])=[C:2]([CH3:3])[CH:1]=[C:9]([CH3:7])[C:15]=4[CH3:16])=[CH:27][CH:28]=3)[C:23]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:22]=2[CH:21]=1

参加物

7

反応物 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 16213799(2,3,5,6-Tetramethylphenyl)boronic acidHCID 534239202,7-Dibromo-9,9-diheptyl-9H-fluorene

生成物 1

HCID 58729335HCID 58729335、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

0.04 mol of durylboronic acid is initially charged in a 1-liter 3-neck flask with 600 ml of toluene, admixed with 0.04 mol of propane-1,3-diol and heated on a water separator until no further water is separated out. Afterward, the water separator is removed and replaced by a reflux condenser, and 0.01 mol of 2,7-dibromo-9,9-diheptylfluorene and 11.6 g of potash dissolved in 42 ml of water are added to the reaction mixture. The flask is then repeatedly evacuated under reduced pressure and flooded with argon in order to add the catalyst, tetrakis(triphenylphosphine)palladium. Finally, the mixture is heated to 110° C. for 48 h and purged with argon during this time. For workup, the organic phase is washed repeatedly with water, extracted and concentrated to dryness. The residue is washed in methanol and filtered off with suction. The crude product is purified by chromatography on silica gel by means of cyclohexane.

後処理

  1. customis separated out
  2. customAfterward, the water separator is removed
  3. customreplaced by a reflux condenser
  4. additionare added to the reaction mixture
  5. customThe flask is then repeatedly evacuated under reduced pressure
  6. additionto add the catalyst, tetrakis(triphenylphosphine)palladium
  7. custompurged with argon during this time
  8. washFor workup, the organic phase is washed repeatedly with water
  9. extractionextracted
  10. concentrationconcentrated to dryness
  11. washThe residue is washed in methanol
  12. filtrationfiltered off with suction
  13. customThe crude product is purified by chromatography on silica gel by means of cyclohexane

出典と根拠

ORDレコード
ord-2418f3247d5d47709a2ef66e614d261e
出典データセット
uspto-grants-2011_05
特許番号
US07951874B2

反応ノート

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