Sodium Hydroxide → HCID 70569336, compound

HRID 1680227Notes

Reaction equation

HRID 1680227 reaction equation
[CH3:1][Li].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C@H:10]3[N:22]([CH3:23])[CH2:21][CH2:20][C@:16]45[C:17]=2[C:18]=1[O:19][CH:15]4[C:14](=[O:24])[CH:13]=[CH:12][C@@:11]35[O:25][CH3:26].[Cl-].[NH4+].[OH-].[Na+]>O1CCCC1.C(OCC)C.[Cu](I)I>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C@H:10]3[N:22]([CH3:23])[CH2:21][CH2:20][C@:16]45[C:17]=2[C:18]=1[O:19][CH:15]4[C:14](=[O:24])[CH2:13][C@@H:12]([CH3:1])[C@@:11]35[O:25][CH3:26]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 56990704HCID 56990704, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 70569336HCID 70569336, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of copper iodide (10.49 g, 57.3 mmol) in dry tetrahydrofuran (50 ml) and diethyl ether (50 ml), cooled in an ice bath, methyl lithium (60 ml of a 1.84 molar solution, 0.11 mol) was added under a nitrogen atmosphere. After 10 minutes, a solution of 14-methoxycodeinone (14) (15.0 g, 45.8 mmol) in tetrahydrofuran (300 ml) was added and the mixture was stirred for another 3 hours. At the end of this period, a saturated solution of ammonium chloride (200 ml) was added slowly. This was followed by the addition of a 20% NaOH solution until the mixture was basic. The aqueous layer was separated and extracted with ethyl acetate (3×100 ml) whereupon the organic extracts were combined, washed once with water (100 ml), dried over MgSO4, filtered and evaporated to give crude (20). This material was recrystallized from ethanol to give 8 g (51% theory) of the title compound as a colorless solid, m.p. 204°-205° C.

Workup

  1. temperaturecooled in an ice bath
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×100 ml) whereupon the organic extracts
  4. washwashed once with water (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-811e803512ad40aa856d5b13ff9bf663
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

Loading…