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

HRID 234666

반응식

HRID 234666 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4850ab2726cd4a8db7991140b840ee6a
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05595989

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