1-Bromopropane → HCID 13772986, compound

HRID 746006Notes

Reaction equation

HRID 746006 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[Mg].[CH2:6]([N:8]1[C:16]2[CH:15]=[C:14]3[CH:17]=[CH:18][C:19]([O:23][CH3:24])=[C:20]([O:21][CH3:22])[C:13]3=[C:12]3[CH:25]=[C:26]([CH3:28])[CH:27]=[C:10]([C:11]=23)[C:9]1=[O:29])[CH3:7]>O1CCCC1>[CH2:6]([N:8]1[C:16]2[CH:15]=[C:14]3[CH:17]=[CH:18][C:19]([O:23][CH3:24])=[C:20]([O:21][CH3:22])[C:13]3=[C:12]3[CH:25]=[C:26]([CH3:28])[CH:27]=[C:10]([C:11]=23)[C:9]1([OH:29])[CH2:1][CH2:2][CH3:3])[CH3:7]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 5462224MagnesiumHCID 13772985HCID 13772985, compound

Product 1

HCID 13772986HCID 13772986, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 377 ml (4.1M) of n-propyl bromide in 4 liters tetrahydrofuran is added over a period of 90 minutes at reflux to 99.8 g (4.1M) of magnesium turnings and the mixture is stirred for one hour at reflux. To the resultant mixture is added dropwise over 30 minutes and under a nitrogen atmosphere a solution of 880 g (2.73M) of 5-ethyl-4,5-dihydro-9,10-dimethoxy-2-methyl-4-oxo-dibenz[cd,f]indole in 6 liters tetrahydrofuran. The reaction mixture is warmed for 2 hours at reflux and then extracted with methylene chloride. The organic phase is washed with a saturated solution of potassium bicarbonate and with water, dried over sodium sulfate and evaporated to give the title compound in the form of a red-brown oil [IR Spectrum (CH2Cl2): 3540 cm-1 (OH)]. The crude product is directly used for the next step.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture is warmed for 2 hours
  3. temperatureat reflux
  4. extractionextracted with methylene chloride
  5. washThe organic phase is washed with a saturated solution of potassium bicarbonate and with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d09f1605e41b436fac6a511787a332ff
Source dataset
uspto-grants-1986_07
Patent number
US04602032

Reaction notes

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