HCID 57849005, compound → HCID 57849018, compound

HRID 736456Notes

Reaction equation

HRID 736456 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8]/[C:9](=[C:12]1\[CH2:13][O:14][C:15]2[C:20]([C:21]\1=[O:22])=[CH:19][C:18]([F:23])=[CH:17][CH:16]=2)/SC.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCOCC>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8]/[C:9](=[C:12]1\[CH2:13][O:14][C:15]2[C:20]([C:21]\1=[O:22])=[CH:19][C:18]([F:23])=[CH:17][CH:16]=2)/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 57849005HCID 57849005, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 57849018HCID 57849018, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 650 mg (1.92 mmol) 5-2 in 50 mL of Et2O cooled to 0° C. was added dropwise 670 μL (2.02 mmol) 3M PhMgBr in Et2O. This mixture was stirred for 30 min, quenched with a solution of saturated NH4Cl, dumped into a separatory funnel containing EtOAc, the layers were separated, and the organic phase was washed with brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel chromatography with EtOAc/hexanes to provide 5-3 as a yellow oil. Data for 5-3: 1HNMR (500 MHz, CDCl3) δ 7.65 (m, 1H), 7.5-7.3 (m, 4H), 7.15 (m, 2H), 6.85 (m, 1H), 4.8 (s, 2H), 4.55 (m, 1H), 4.05 (m, 2H), 3.7 (m, 2H), 3.0 (m, 2H), 2.0 (m, 1H), 1.7 (m, 2H), 1.3 (m, 1H) ppm, LC-MS: rt=2.9 min, m/z=369 (M+1).

Workup

  1. customquenched with a solution of saturated NH4Cl
  2. customdumped into a separatory funnel
  3. additioncontaining EtOAc
  4. customthe layers were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography with EtOAc/hexanes

Sources & evidence

ORD record
ord-1a5b8699e8214d7e8f682451fc0d41ec
Source dataset
uspto-grants-2009_09
Patent number
US07595337B2

Reaction notes

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