Sodium Carbonate → HCID 89581294, compound

HRID 1501169Notes

Reaction equation

HRID 1501169 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1OC(C)(C)C(C)(C)O1.BrC1[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 11334366Tert-butyl 4-bromobenzoateHCID 12215377HCID 12215377, compound

Product 1

HCID 89581294HCID 89581294, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(furan-2-yl)-4,4,5,5-tetramethyl-1,3-dioxolane (500 mg, 2.6 mmol), tert-butyl 4-bromobenzoate (512 mg, 2 mmol) and sodium carbonate (636 mg, 6 mmol), tetra(triphenylphosphine) palladium (115 mg, 0.1 mmol) in mixed solution of 1,4-dioxane (20 ml) and water (4 ml) was stirred for 15 hours at 90° C. under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to give tert-butyl 4-(furan-2-yl)benzoate (400 mg, 82%) as a yellow oil. LRMS (M+H+) m/z: calcd 244.11. found 244. 1H NMR (300 MHz, CD3OD): δ 7.99-7.96 (m, 2H), 7.78-7.75 (m, 2H), 7.63-7.62 (m, 1H), 6.94-6.93 (m, 1H), 6.57-6.56 (m, 1H), 1.61 (s, 9H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customto give a residue
  4. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-f11a0268f1de41399b69fdd915cfb825
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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