HCID 89649135, compound → HCID 89648565, compound

HRID 1773979Notes

Reaction equation

HRID 1773979 reaction equation
[Cl-].[C:2]([O:6][C:7](=[O:10])[CH2:8][Zn+])([CH3:5])([CH3:4])[CH3:3].[CH2:11]([O:18][C:19]1[CH:24]=[C:23](Br)[CH:22]=[CH:21][C:20]=1[CH:26]=[CH:27][CH3:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:2]([O:6][C:7](=[O:10])[CH2:8][C:23]1[CH:22]=[CH:21][C:20]([CH:26]=[CH:27][CH3:28])=[C:19]([O:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:24]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 89649135HCID 89649135, compoundHCID 178451183HCID 178451183, compound

Product 1

HCID 89648565HCID 89648565, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-tert-butoxy-2-oxoethylzinc chloride (12.2 mL, 6.13 mmol, 1.8 eq.) was added to a solution of 2-benzyloxy-4-bromo-1-(propenyl)-benzene (mixture of E- and Z-isomers ca. 9:1) (1.17 g, 3.40 mmol, 1.00 eq.) and bis(tri-tert-butylphosphine)palladium(0) (266 mg, 0.51 mmol, 0.15 eq.) in dioxane (27 mL). The resulting mixture was stirred at r.t. for 18 hours. The mixture was filtered through Celite and the filter cake was rinsed with dioxane. The filtrate was concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane 100% to Heptane+12% AcOEt) to yield [3-benzyloxy-4-(propenyl)-phenyl]-acetic acid tert-butyl ester as a pale yellow oil.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was rinsed with dioxane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane 100% to Heptane+12% AcOEt)

Sources & evidence

ORD record
ord-7482abd01c314ddcafdf2f48a39b31e4
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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