HCID 57849366, compound → HCID 57849312, compound

HRID 736528Notes

Reaction equation

HRID 736528 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:25]2[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])=[C:27]([CH3:38])[CH:26]=2)([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][C:15]=1[CH3:39])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:25]2[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([OH:35])([CH:1]([CH3:3])[CH3:2])[CH:32]([CH3:33])[CH3:34])=[C:27]([CH3:38])[CH:26]=2)([CH2:21][CH3:22])[CH2:23][CH3:24])=[CH:16][C:15]=1[CH3:39])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 57849366HCID 57849366, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57849312HCID 57849312, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Anhydrous CeCl3 (0.82 g) is suspended in THF (30 mL) with stirring overnight. It is cooled to 0° C., treated with 2.0 M iPrMgCl (1.3 mL) and stirred at 0° C. for 1 h. A solution of 1-{4-[1-(4-benzyloxy-3-methyl-phenyl)-1-ethyl-propyl]-2-methyl-phenoxy}-3-methyl-butan-2-one (1.01 g, 2.21 mmol) in THF (10 mL) is added. The mixture is stirred at 0° C. for 1 h, before it is quenched with 0.1 M HCl (20 mL). It is extracted with EtOAc (200 mL), washed with 0.1 M HCl (3×50 mL); MgSO4 dried and concentrated to give the title compound (1.10 g, 2.19 mmol, 99%). 1H NMR (CDCl3), δ 0.62 (t, J=7.0 Hz, 6H), 1.01 (d, J=7.1 Hz, 6H), 1.04 (d, J=7.1 Hz, 6H), 1.57 (b, 2H), 2.04 (q, J=7.0 Hz, 4H), 2.17 (s, 3H), 2.24 (s, 3H), 3.88 (s, 2H), 5.04 (s, 2H), 6.70 (d, J=8.3 Hz, 1H), 6.77 (d, J=9.2 Hz, 1H), 6.90 (d, J=2.2 Hz, 1H), 6.93-6.98 (m, 3H), 7.29-7.47 (m, 5H).

Workup

  1. stirringstirred at 0° C. for 1 h
  2. stirringThe mixture is stirred at 0° C. for 1 h, before it
  3. customis quenched with 0.1 M HCl (20 mL)
  4. extractionIt is extracted with EtOAc (200 mL)
  5. washwashed with 0.1 M HCl (3×50 mL)
  6. dry with materialMgSO4 dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-23a43f09cdee45238b433a1bebe28494
Source dataset
uspto-grants-2009_09
Patent number
US07595345B2

Reaction notes

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