Ethyl Acetate → HCID 11181172, compound

HRID 1829627Notes

Reaction equation

HRID 1829627 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C@H:14]([O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)#[CH:2].I[C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1.[NH4+].[Cl-].C(OCC)(=O)C>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Si:23]([O:22][C@@H:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C@@H:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH3:5])[C@H:6]3[CH2:7][CH2:8][C@@H:3]2[C:1]#[C:2][C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)[CH2:13]1)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 122074-IodotolueneHCID 25517Ammonium ChlorideHCID 11455482HCID 11455482, compound

Product 1

HCID 11181172HCID 11181172, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent2×

Procedure

A solution of 17β-ethynyl-3α-(t-butyidiphenylsilyloxy)-5α-androstane (120 mg, 0.23 mmol) in pyrrolidine (2 mL) was added to a mixture of tetrakis triphenylposphine palladium (0) (13.28 mg, 0.0115 mmol) and CuI (4.4 mg, 0.023 mmol) in pyrrolidine (1 mL). To the resulting mixture was added 4-iodotoluene (150 mg, 0.69 mmol) and was stirred at RT for 24 h. Addition of saturated aqueous NH4Cl solution followed by ethyl acetate. Extraction of the organic layer with water and brine and drying (Na2SO4) followed by evaporation of the solvent in vacuo and subsequent purification of the residue with flash column chromatography using petroleum ether/acetone 80/20 as eluent afforded the desired compound named above.

Workup

  1. extractionExtraction of the organic layer with water and brine
  2. dry with materialdrying (Na2SO4)
  3. customfollowed by evaporation of the solvent in vacuo and subsequent purification of the residue with flash column chromatography

Sources & evidence

ORD record
ord-ccf52b92abbf4d398cd9ddc8e45d456e
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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