HCID 57849324, compound → HCID 57849366, compound

HRID 736527Notes

Reaction equation

HRID 736527 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:33]=[CH:32][C:23]([O:24][CH2:25][C:26](N(OC)C)=[O:27])=[C:22]([CH3:34])[CH:21]=2)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:36]([Mg]Cl)([CH3:38])[CH3:37]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:33]=[CH:32][C:23]([O:24][CH2:25][C:26](=[O:27])[CH:36]([CH3:38])[CH3:37])=[C:22]([CH3:34])[CH:21]=2)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 57849324HCID 57849324, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57849366HCID 57849366, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 2-{4-[1-(4-benzyloxy-3-methyl-phenyl)-1-ethyl-propyl]-2-methyl-phenoxy}-N-methoxy-N-methyl-acetamide (2.36 g, 4.98 mmol) in THF (50 mL) is added 2.0 M iPrMgCl (3.0 mL, 5.98 mmol). The reaction is stirred at 0° C. for 30 m, then at RT for 1 h. It is quenched with satd NH4Cl (20 mL), diluted with H2O (50 mL), extracted with EtOAc (2×100 mL), washed with 0.1 M HCl (50 mL), H2O (50 mL); MgSO4 dried, concentrated and purified to give the title compound (1.01 g, 2.21 mmol, 44%).

Workup

  1. customIt is quenched with satd NH4Cl (20 mL)
  2. additiondiluted with H2O (50 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. washwashed with 0.1 M HCl (50 mL), H2O (50 mL)
  5. dry with materialMgSO4 dried
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-ce28f0c15fe34b44bc9b70fa1d0b80da
Source dataset
uspto-grants-2009_09
Patent number
US07595345B2

Reaction notes

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