Ammonium Chloride → 5,7-dimethyl-8-methoxy-9-(2,2-diethoxyethyl)-1,2,3,4-tetrahydro-9H-fluorene

HRID 2051419Notes

Reaction equation

HRID 2051419 reaction equation
CCCCCC.C([Li])CCC.[CH3:12][C:13]1[CH:25]=[C:24]([CH3:26])[C:23]([O:27][CH3:28])=[C:22]2[C:14]=1[CH:15]1[C:20](=[CH:21]2)[CH2:19][CH2:18][CH2:17][CH2:16]1.[CH2:29]([O:31][CH:32]([O:35][CH2:36][CH3:37])[CH2:33]Br)[CH3:30].[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[CH3:12][C:13]1[CH:25]=[C:24]([CH3:26])[C:23]([O:27][CH3:28])=[C:22]2[C:14]=1[C:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=1[CH:21]2[CH2:33][CH:32]([O:35][CH2:36][CH3:37])[O:31][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 151571995,7-dimethyl-8-methoxy-2,3,4,4a-tetrahydro-1H-fluoreneHCID 178418244HCID 178418244, compound

Product 1

HCID 151572005,7-dimethyl-8-methoxy-9-(2,2-diethoxyethyl)-1,2,3,4-tetrahydro-9H-fluorene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

19 Milliliters of a 15% n-butyl lithium n-hexane solution was added dropwise to a tetrahydrofuran solution containing 5.0 g of 5,7-dimethyl-8-methoxy-2,3,4,4a-tetrahydro-1H-fluorene in 50 ml of tetrahydrofuran at -50° C. After stirring at the same temperature for 40 minutes, thereto was added dropwise 6 ml of bromoacetoaldehyde diethyl acetal at the same temperature, followed by stirring at the same temperature for 1.5 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution and this was diluted with diethyl ether, washed with water twice and then with a saturated aqueous sodium chloride solution and then dried with magnesium sulfate. The solvent was distilled off and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:30) to obtain 5.68 g of 5,7-dimethyl-8-methoxy-9-(2,2-diethoxyethyl)-1,2,3,4-tetrahydro-9H-fluorene.

Workup

  1. stirringby stirring at the same temperature for 1.5 hour
  2. washwashed with water twice
  3. dry with materialwith a saturated aqueous sodium chloride solution and then dried with magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:30)

Sources & evidence

ORD record
ord-3025bbbc50bf4fa79ac1dfeefed9a1fe
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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