1,2-Dibromoethane → HCID 69998640, compound

HRID 1859481Notes

Reaction equation

HRID 1859481 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][CH2:4][Mg]I.ICCC(C)C.[Mg].BrCCBr.[C:19]([O:27][C@H:28]1[CH2:48][CH2:47][C@@:46]2([CH3:49])[C@@H:30]([CH2:31][CH2:32][C:33]3[C:34]4[C@:42]([CH3:50])([CH2:43][CH2:44][C:45]=32)[C@@H:37]([C@@H:38]([CH:40]=[O:41])[CH3:39])[CH2:36][CH:35]=4)[C:29]1([CH3:52])[CH3:51])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>C(OCC)C.C1COCC1>[C:19]([O:27][C@H:28]1[CH2:48][CH2:47][C@@:46]2([CH3:49])[C@@H:30]([CH2:31][CH2:32][C:33]3[C:34]4[C@:42]([CH3:50])([CH2:43][CH2:44][C:45]=32)[C@@H:37]([C@H:38]([CH3:39])[C@@H:40]([OH:41])[CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1])[CH2:36][CH:35]=4)[C:29]1([CH3:51])[CH3:52])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 6

HCID 78391,2-DibromoethaneHCID 109241-Iodo-3-methylbutaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 56994186HCID 56994186, compoundHCID 178445871HCID 178445871, compound

Product 1

HCID 69998640HCID 69998640, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

i)—A solution of 3-methylbutylmagnesium iodide (12 ml), prepared from 1-iodo-3-methylbutane (2.36 ml) and magnesium (0.48 g), activated with 1,2-dibromoethane (0.040 ml), in diethyl ether (10 ml and 10 ml, respectively) at reflux temperature, was added dropwise to (3β,5α,20S)-3-(benzoyloxy)-4,4-dimethylpregna-8,14-diene-20-carboxaldehyde (WO-09852965; 1.55 g) in THF (20 ml). The reaction mixture was stirred at room temperature for 45 min. and then poured into a saturated aqueous solution of ammonium chloride. The product was extracted into ethyl acetate; the combined organic phases were washed with a saturated aqueous solution of ammonium chloride and with brine, dried over magnesium sulfate and concentrated under reduced pressure. Column chromatography afforded (3β,5α,20S,22S)-4,4-dimethylcholesta-8,14-diene-3,22-diol 3-benzoate (1.1 g).

Workup

  1. temperaturerespectively) at reflux temperature
  2. extractionThe product was extracted into ethyl acetate
  3. washthe combined organic phases were washed with a saturated aqueous solution of ammonium chloride and with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e01d0bf09494ca38e0aba69185f08dd
Source dataset
uspto-grants-2003_03
Patent number
US06528501B1

Reaction notes

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