Ammonium Chloride → HCID 18917159, compound

HRID 861896Notes

Reaction equation

HRID 861896 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH:6]1[C:16]2[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[C:13](=[O:21])[C:12]3[CH:22]=[CH:23][CH:24]=[CH:25][C:11]=3[C:10]=2[CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+]>O1CCCC1>[CH:1]1([C:13]2([OH:21])[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[C:16]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C:11]3[CH:25]=[CH:24][CH:23]=[CH:22][C:12]2=3)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 12437220HCID 12437220, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 18917159HCID 18917159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of cyclopropylmagnesium bromide in dry tetrahydrofuran (prepared from cyclopropylbromide (4.54 g, 37.5 mmol), magnesium turnings (0.91 g, 37.5 mmol) and dry tetrahydrofuran (30 ml)) was placed under an atmosphere of nitrogen. A solution of 9H-tribenzo[a,c,e]cyclohepten-9-one (1.92 g, 7.5 mmol) (prepared according to W. Tochtermann, Chem. Ber., 97, 1329 (1964)) in tetrahydrofuran (20 ml) was added dropwise and when addition was complete the mixture was heated at reflux temperature for 30 minutes. The reaction mixture was cooled on an ice-bath and saturated ammonium chloride (50 ml) was added carefully. The organic layer was separated and the aqueous phase extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (MgSO4) and the solvent was evaporated in vacuo affording 2.69 g of 9-cyclopropyl-9H-tribenzo[a,c,e]cyclohepten-9-ol.

Workup

  1. additionwhen addition
  2. temperaturewas heated
  3. temperatureat reflux temperature for 30 minutes
  4. temperatureThe reaction mixture was cooled on an ice-bath
  5. customThe organic layer was separated
  6. extractionthe aqueous phase extracted with diethyl ether (2×100 ml)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-299137ccb1214c28bf79643d1af7252d
Source dataset
uspto-grants-1998_02
Patent number
US05716949

Reaction notes

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