1-(4-Iodophenyl)ethan-1-one → HCID 69904757, compound

HRID 1837115Notes

Reaction equation

HRID 1837115 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1)=[O:3].[OH:11][C@:12]1([CH3:35])[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:26]2[CH2:25][CH2:24][C@@:22]2([CH3:23])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[O:31][CH2:32][C:33]#[CH:34])[CH2:13]1>>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:34]#[C:33][CH2:32][O:31][C@H:21]2[CH2:20][CH2:19][C@H:18]3[C@H:17]4[C@H:26]([CH2:25][CH2:24][C@:22]23[CH3:23])[C@:27]2([CH3:30])[C@H:14]([CH2:13][C@@:12]([OH:11])([CH3:35])[CH2:29][CH2:28]2)[CH2:15][CH2:16]4)=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

3

Reactant 2

HCID 728691-(4-Iodophenyl)ethan-1-oneHCID 86754249HCID 86754249, compound

Product 1

HCID 69904757HCID 69904757, compoundYield 68.4%

Conditions

Temperature
23 °C

Procedure

A solution of 4-iodoacetophenone (16 mg, 0.06 mmol), 3α-hydroxy-3β-methyl-17β-(2-propynyloxy)-5α-androstane (22 mg, 0.06 mmol) in dry degassed triethylamine (1 mL) was stirred under argon at 23° C. Bis(triphenylphosphine)palladium chloride (2 mg) and CuI (2 mg) were added and the mixture was stirred at this temp. for 45 min. CH2Cl2 (4 mL) was added and the mixture was stirred at 23° C. for 1 hr. The TLC showed 100% conversion of the starting material, hence, the solvent was removed and the residue was purified by chromatography on silica gel. Elution with hexane:acetone (85:15) gave 17β-[3-(4-acetylphenyl)-2-propynyloxy]-3α-hydroxy-3β-methyl-5α-androstane (19 mg) as a colorless solid; mp 52-55° C.; TLC Rf (hexane:acetone 85:15)=0.15.

Workup

  1. customdegassed triethylamine (1 mL)
  2. additionBis(triphenylphosphine)palladium chloride (2 mg) and CuI (2 mg) were added
  3. stirringthe mixture was stirred at this temp
  4. additionCH2Cl2 (4 mL) was added
  5. stirringthe mixture was stirred at 23° C. for 1 hr
  6. customhence, the solvent was removed
  7. customthe residue was purified by chromatography on silica gel
  8. washElution with hexane:acetone (85:15)

Sources & evidence

ORD record
ord-4738147e909443af8735117b712a0bf6
Source dataset
uspto-grants-2004_08
Patent number
US06780853B1

Reaction notes

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