Carbon tetrabromide → HCID 11331470, compound

HRID 1829625Notes

Reaction equation

HRID 1829625 reaction equation
[Br:1][C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Si:25]([O:42][C@@H:43]1[CH2:60][CH2:59][C@@:58]2([CH3:61])[C@@H:45]([CH2:46][CH2:47][C@@H:48]3[C@@H:57]2[CH2:56][CH2:55][C@@:53]2([CH3:54])[C@H:49]3[CH2:50][CH2:51][C@@H:52]2[CH:62]=O)[CH2:44]1)([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]([Br:5])=[CH:62][C@H:52]1[CH2:51][CH2:50][C@H:49]2[C@H:48]3[C@H:57]([CH2:56][CH2:55][C@:53]12[CH3:54])[C@:58]1([CH3:61])[C@H:45]([CH2:44][C@H:43]([O:42][Si:25]([C:38]([CH3:39])([CH3:41])[CH3:40])([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:60][CH2:59]1)[CH2:46][CH2:47]3

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86600183HCID 86600183, compound

Product 1

HCID 11331470HCID 11331470, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tetrabromomethane (1.99 g, 6 mmol) in anhydrous methylene chloride (31 mL) was added at 0° C., triphenylphosphine (3.14 g, 6 mmol) and the resulting mixture is stirred for 10 min. Subsequently, a solution of 3α-(t-butyidiphenylsilyloxy)-5α-androstan-17β-carboxaldehyde (540 mg, 1 mmol) in methylene chloride (6 mL) was added and the mixture was stirred at 0° C. for an additional 10 min. The reaction mixture was diluted with ethyl acetate and the organic layer is washed with water, saturated aqueous NaCl solution and was dried with anhydrous Na2SO4. The solvent was evaporated in vacuo and the residue was purified with flash column chromatography using petroleum ether/ether 95/5 as eluent afforded the desired compound named.

Workup

  1. washthe organic layer is washed with water, saturated aqueous NaCl solution
  2. dry with materialwas dried with anhydrous Na2SO4
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified with flash column chromatography

Sources & evidence

ORD record
ord-04147175942446a1bba137c509668cf6
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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