Hexane → HCID 70635033, compound

HRID 1606360Notes

Reaction equation

HRID 1606360 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CCCCCC.[O:12]1[C@H:14]2[CH2:15][C@H:16]3[C@:31]([CH3:33])([CH2:32][C@@H:13]12)[C@@H:30]1[C@H:19]([C@H:20]2[C@:27]([CH3:35])([CH2:28][C:29]1=[O:34])[C@@H:23]([C:24](=[O:26])[CH3:25])[CH2:22][CH2:21]2)[CH2:18][CH2:17]3.[Cl-].[NH4+]>CCOCC>[CH2:1]([C@H:13]1[CH2:32][C@@:31]2([CH3:33])[C@@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:30]2[C:29](=[O:34])[CH2:28][C@@:27]2([CH3:35])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C:24](=[O:26])[CH3:25])[CH2:15][C@@H:14]1[OH:12])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 86733130HCID 86733130, compoundHCID 178418339Butyllithium

Product 1

HCID 70635033HCID 70635033, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 2 molar solution of n-butyl lithium in hexane (30 ml., 60mmole) was added to a stirred suspension of cuprous iodide (5.7 g., 30 mmole) in dry ether (90 ml.) under nitrogen at -20°. A cold solution of 2α,3α-epoxy-5α-pregnane-11,20-dione (1.65 g., 5 mmole) in dry ether (260 ml.) was then added and the mixture was maintained at 0° for 70 hr. The reaction mixture was then poured into aqueous ammonium chloride solution and extracted into ethyl acetate.

Workup

  1. temperaturethe mixture was maintained at 0° for 70 hr
  2. extractionextracted into ethyl acetate

Sources & evidence

ORD record
ord-64974fc1f75e41509c68cc71722e40dc
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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