Diethyl Ether → HCID 25241851, compound

HRID 2406860Notes

Reaction equation

HRID 2406860 reaction equation
[Mg+2].[Br-].[Br-].CCOCC.C(N(C(C)C)CC)(C)C.[C:18]([C:21]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH:22]=1)([CH3:20])=[CH2:19].C[O:28][C:29](=O)[CH:30]=[CH2:31]>C(Cl)Cl>[CH3:19][C:18]1[CH2:20][CH2:31][C@@H:30]2[C@@H:22]3[C:21]=1[CH2:25][CH2:24][C@@H:23]3[O:26][C:29]2=[O:28]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 7294Methyl AcrylateHCID 81531DiisopropylethylamineHCID 82241Magnesium BromideHCID 56590408HCID 56590408, compound

Product 1

HCID 25241851HCID 25241851, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Anhydrous MgBr2.Et2O (759.2 mg, 2.940 mmol) was suspended in DCM (3.5 mL), treated with Diisopropylethylamin (1.0, 760 mg, 5.880 mmol) and stirred for 15 minutes until the suspension turns magenta. Then compound (7a) (182.4 mg, 1.469 mmol) dissolved in DCM (11.5) was added slowly within 15 minutes. After stirring for 1 hour Methylacrylate (0.27 mL, 257.9 mg, 2.995 mmol) was added dropwise. The resulting mixture was stirred for 5½ hours before it was quenched with saturated aqueous NH4Cl. For a better phase separation potassium sodium tartrate was added and the solution extracted with DCM (4×). The combined extracts were dried (Na2SO4) and concentrated in vacuo. Purification by chromatography (hexane/EtOAc 6/1) furnished 194.3 mg of compound (8a) as white solid with 74% yield.

Workup

  1. additionwas added slowly within 15 minutes
  2. additionwas added dropwise
  3. stirringThe resulting mixture was stirred for 5½ hours before it
  4. customwas quenched with saturated aqueous NH4Cl
  5. customFor a better phase separation potassium sodium tartrate
  6. additionwas added
  7. extractionthe solution extracted with DCM (4×)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customPurification by chromatography (hexane/EtOAc 6/1)

Sources & evidence

ORD record
ord-a7bc45d740754ce9b20c2a77e2fa7f09
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

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