HCID 89648565, compound → HCID 89648566, compound

HRID 1773980Notes

Reaction equation

HRID 1773980 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][CH3:16])=[C:10]([O:17]CC2C=CC=CC=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:5][C:6](=[O:25])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[C:10]([OH:17])[CH:9]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 89648565HCID 89648565, compound

Product 1

HCID 89648566HCID 89648566, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-benzyloxy-4-(propenyl)-phenyl]-acetic acid tert-butyl ester (1.21 g, 3.21 mmol, 1 eq.) in THF (39 mL) under N2, palladium on activated carbon (10% wt., 121 mg) was added. The flask was carefully evacuated and refilled with H2 (3×). The black suspension was stirred at r.t. under an H2-atmosphere for 18 hours. The black suspension was filtered through Celite and the filter cake was rinsed with THF. The filtrate was concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 50 fractions of 45 mL, Heptane 100% to Heptane+20% AcOEt) to yield the title compound as a colorless oil.

Workup

  1. customThe flask was carefully evacuated
  2. additionrefilled with H2 (3×)
  3. filtrationThe black suspension was filtered through Celite
  4. washthe filter cake was rinsed with THF
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 50 fractions of 45 mL, Heptane 100% to Heptane+20% AcOEt)

Sources & evidence

ORD record
ord-4a5185bb18a041fcb2c8d76275522343
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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