5H-Dibenzo[a,d]cyclohepten-5-one → 5-cyclopropyl-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 234666

反応式

HRID 234666 の反応式
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH:6]1[C:16]2[CH:15]=[CH:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+]>C1COCC1.O>[CH:1]1([C:11]2([OH:21])[C:12]3[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=3[CH:14]=[CH:15][C:16]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]2=3)[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 25517Ammonium ChlorideHCID 178418630HCID 178418630、化合物

生成物 1

HCID 187993385-cyclopropyl-5H-dibenzo[a,d]cyclohepten-5-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of cyclopropylmagnesium bromide in dry THF (prepared from cyclopropylbromide (8.0 g, 0.067 mol), magnesium turnings (1.3 g, 0.053 mol) and dry THF (35 ml)) was placed under an atmosphere of nitrogen. A solution of 5H-dibenzo[a,d]cyclohepten-5-one (6.0 g, 0.028 mol) in dry THF (15 ml) was added dropwise and when addition was complete the mixture was heated at reflux for 30 minutes. The reaction mixture was cooled on an ice-bath and saturated ammonium chloride (35 ml) was carefully added. The mixture was diluted with water (50 ml) and extracted with diethyl ether (2×50 ml). The combined organic extracts were washed with water, dried (Na2SO4) and the solvent was evaporated in vacuo to give 8.6 g of crude 5-cyclopropyl-5H-dibenzo[a,d]cyclohepten-5-ol.

後処理

  1. additionwhen addition
  2. temperaturewas heated
  3. temperatureat reflux for 30 minutes
  4. temperatureThe reaction mixture was cooled on an ice-bath
  5. extractionextracted with diethyl ether (2×50 ml)
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-4850ab2726cd4a8db7991140b840ee6a
出典データセット
uspto-grants-1997_01
特許番号
US05595989

関連ノート

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