Ammonium Chloride → HCID 86733297, compound

HRID 1606363Notes

Reaction equation

HRID 1606363 reaction equation
[CH3:1][Li].[CH2:3]([O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:27])[CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH:15]=[C:16]2[C:17](=[O:19])[CH3:18])[CH2:8][C@@H:7]1[OH:29])[CH3:4].[Cl-].[NH4+]>CCOCC.O1CCCC1>[CH2:3]([O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:27])[CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][C@@H:15]([CH3:1])[C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8][C@@H:7]1[OH:29])[CH3:4]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 86733298HCID 86733298, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 86733297HCID 86733297, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyllithium in ether (c. 2M 4 ml.) was added to a stirred slurry of cuprous iodide (630 mg.) in dry ether (60 ml.) under dry nitrogen until the initially formed yellow precipitate redissolved. A solution of 2β-ethoxy- 3α-hydroxy-5α-pregn-16-ene11,20-dione (420 mg.) in dry tetrahydrofuran (35 ml.) was added to the stirred solution at 0° and stirring was continued, at 0°, for 30 minutes. The mixture was then poured into saturated ammonium chloride solution (150 ml.), more ether (150 ml.) was added, the organic layer separated, washed with saturated ammonium chloride solution (150 ml.) and water (150 ml.) and dried (Na2 SO4). The solution was then evaporated. The residue was purified by preparative TLC (CHCl3 × 4). The least polar component was recrystallised from acetone/petrol to give title compound (130 mg.) as white needles; m.p. 178°-179°; [α]D + 112° (c 0.3).

Workup

  1. dissolutionredissolved
  2. additionwas added
  3. customthe organic layer separated
  4. washwashed with saturated ammonium chloride solution (150 ml.) and water (150 ml.)
  5. customdried (Na2 SO4)
  6. customThe solution was then evaporated
  7. customThe residue was purified by preparative TLC (CHCl3 × 4)
  8. customThe least polar component was recrystallised from acetone/petrol

Sources & evidence

ORD record
ord-0b5d1d7bae4e499b89cded79d6b0a22b
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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