Diethyl Ether → HCID 68704484, compound

HRID 732317Notes

Reaction equation

HRID 732317 reaction equation
C[O:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[O:11][CH:10]([C:15]3[CH:20]=[CH:19][C:18](OCOC)=[CH:17][CH:16]=3)C3CC(O)CC3[C:7]=2[CH:6]=1.C([Mg]Cl)C=C.CC[O:36]CC.C([O-])(O)=O.[Na+].[CH2:44]([CH:46]1[CH2:72][CH:49]2[CH:50](C3C=CC(OCOC)=CC=3)[O:51][C:52]3[CH:53]=CC(OCOC)=CC=3C2C1)[CH3:45]>C1COCC1>[CH2:52]([O:51][C:50]([CH:49]1[CH:72]([CH2:46][CH:44]=[CH2:45])[C:6]2[C:5](=[CH:14][CH:13]=[C:12]([O:11][CH2:10][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:7]=2)[O:4][C:3]1=[O:2])=[O:36])[CH3:53]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 68706007HCID 68706007, compoundHCID 68725707HCID 68725707, compoundHCID 178418473HCID 178418473, compound

Product 1

HCID 68704484HCID 68704484, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0 C solution of Preparation 27 (10.0 g, 30.8 mmol) in THF (125 mL) add a solution of allyl magnesium chloride in Et2O (46 mL, 1.0 M, 46 mmol). Maintain the reaction at 0 C for 30 min, then pour the reaction contents into a solution of ½ satd. NaHCO3 (250 mL). Extract the solution with Et2O (2×150 mL) and EtOAc (150 mL). Wash the combined organic extracts with H2O (150 mL) and brine (150 mL), dry the organics over Na2SO4, and concentrate to afford a brown oil. Purify the product by MPLC (0% to 15% to 25% EtOAc/hexanes) to afford Preparation 38 (7.72 g, 68%) as a light yellow solid. 1H NMR (CDCl3) δ 7.31-7.43 (m, 5H), 7.01 (d, J=8.8 Hz, 1H), 6.87 (dd, J=8.8, 3.0 Hz, 1H), 6.79 (d, J=3.0 Hz, 1H), 5.71 (m, 1H), 5.15 (dd, J=0.8, 9.8 Hz, 1H), 5.10 (dd, J=0.8, 17.6 Hz, 1H), 5.04 (A of AB, JAB=14.2 Hz, 1H), 5.03 (B of AB, JAB=14.2 Hz, 1H), 4.08 (m, 2H), 3.80 (d, J=2.4 Hz, 1H), 3.41 (m, 1H), 2.35 (m, 2H), 1.08 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureMaintain
  2. customthe reaction at 0 C for 30 min
  3. additionpour
  4. customthe reaction contents into a solution of ½
  5. extractionExtract the solution with Et2O (2×150 mL) and EtOAc (150 mL)
  6. washWash the combined organic extracts with H2O (150 mL) and brine (150 mL)
  7. dry with materialdry the organics over Na2SO4
  8. concentrationconcentrate
  9. customto afford a brown oil
  10. customPurify the product by MPLC (0% to 15% to 25% EtOAc/hexanes)
  11. customto afford

Sources & evidence

ORD record
ord-995be24dbe6b4d74a3bf7685cdc78be6
Source dataset
uspto-grants-2009_09
Patent number
US07585985B2

Reaction notes

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