Sodium Carbonate → HCID 89580481, compound

HRID 1501176Notes

Reaction equation

[C:1]1(B2OC(C)(C)C(C)(C)O2)[CH2:5][CH2:4][CH2:3][CH:2]=1.Br[C:16]1[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.O.[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>[C:1]1([C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:18][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mg, 2.6 mmol), tert-butyl 4-bromobenzoate (512 mg, 2 mmol), sodium carbonate (636 mg, 6 mmol) and tetra(triphenylphosphine) palladium (115 mg, 0.1 mmol) in 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-cyclopentenylbenzoate (400 mg, 82%) as a yellow oil. LRMS (M+H+) m/z: calcd 244.15. found 244. 1H NMR (300 MHz, CD3OD): δ 7.94-7.91 (m, 2H), 7.58-7.54 (m, 2H), 6.43-6.42 (m, 1H), 2.78-2.76 (m, 2H), 2.61-2.59 (m, 2H), 2.11-2.08 (m, 2H), 1.64 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-4172d3f0677040b58a968bed8331128c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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