Hydrochloric Acid → 5-Cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 234664

반응식

HRID 234664 반응식
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH:6]1[C:16]2[CH2:15][CH2:14][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+].Cl>C1COCC1>[CH:1]1([C:11]2([OH:21])[C:12]3[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=3[CH2:14][CH2:15][C:16]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]2=3)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14589DibenzosuberoneHCID 25517Ammonium ChlorideHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 192613825-Cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of cyclopropylmagnesium bromide in dry THF (prepared from cyclopropylbromide (12.1 g, 0.10 mol), magnesium turnings (2.45 g, 0.10 mol) and dry THF (65 ml)) was placed under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (10.4 g, 0.05 mol) in dry THF (25 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 (50 ml) was carefully added. The mixture was neutralized with 2N hydrochloric acid and extracted with diethyl ether (2×200 ml). The combined organic extracts were dried (Na2SO4) and the solvent was evaporated in vacuo to give 13.1 g of crude 5-cyclopropyl-10,11-dihydro-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 (2×200 ml)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customthe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-6c81d683fb3144ef90ba2ea1e155f3ba
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05595989

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