Anisole → HCID 18962093, compound

HRID 1707836Notes

Reaction equation

HRID 1707836 reaction equation
[H-].[Na+].[C:3]1([O:9]C)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11]([C:15]1[CH:16]=[C:17]([N:26]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])([CH3:14])([CH3:13])[CH3:12].[H][H].Br[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]Br>CN(C)C=O>[C:22]([C:19]1[CH:18]=[C:17]([N:26]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:27][CH2:28][CH2:29][N:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][N:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:28][CH2:27][N:26]([C:6]2[CH:5]=[C:4]([C:11]([CH3:12])([CH3:13])[CH3:14])[C:3]([OH:9])=[C:8]([C:19]([CH3:18])([CH3:20])[CH3:22])[CH:7]=2)[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:16]=[C:15]([C:11]([CH3:12])([CH3:13])[CH3:14])[C:20]=1[OH:21])([CH3:24])([CH3:25])[CH3:23]

Participants

7

Reactant 5

HCID 7519AnisoleHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 18962104HCID 18962104, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18962093HCID 18962093, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Suspend sodium hydride (48 mg, 2 mmol) and anisole (215 mg, 2 mmol) in anhydrous dimethylformamide (2 mL), cool to 0° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution 1-[(3,5-di-t-butyl-4-hydroxyphenyl)]-1,5-bis(t-butyloxycarbonyl)-1,5-diazapentane (1.91 g, 4 mmol) in dimethylformamide (2 mL). Stir until evolution of hydrogen ceases. Add, by dropwise addition, a solution of 1,5-dibromopentane (230 mg, 1 mmol) in dimethylformamide (2 mL). Stir overnight at room temperature then carefully quench with saturated ammonium chloride. Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound.

Workup

  1. additionAdd, by dropwise addition
  2. additionAdd, by dropwise addition
  3. customthen carefully quench with saturated ammonium chloride
  4. extractionExtract into ethyl acetate
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-ee0bea435bb741f696f093bb0404108c
Source dataset
uspto-grants-1994_10
Patent number
US05354782

Reaction notes

Loading…