Triphenylphosphine → HCID 59648600, compound

HRID 1363284Notes

Reaction equation

HRID 1363284 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.ClC1C=CC(CC2C=C(C=O)SC=2)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O>[CH:9]1([C:2]2[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=2)[CH2:11][CH2:10]1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 75806TricyclohexylphosphineHCID 27570104-Bromo-2-furaldehydeHCID 2760897Cyclopropylboronic acidHCID 596485254-(4-Chlorobenzyl)thiophene-2-carbaldehyde

Product 1

HCID 59648600HCID 59648600, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The title compound was synthesized from 4-bromo-furan-2-carbaldehyde (300 mg, 1.71 mmol) and cyclopropylboronic acid (171 mg, 1.99 mmol), using the conditions to synthesize 4-(4-chlorobenzyl)thiophene-2-carbaldehyde, with the exception that the reaction was run in toluene (7.5 mL) and water (0.5 mL), and triphenylphosphine was replaced with tricyclohexylphosphine (48 mg, 0.17 mmol). Purification by flash chromatography (0-60% EtOAc in heptane) provided 4-cyclopropylfuran-2-carbaldehyde as an orange oil 72 mg (31%). 1H NMR (400 MHz, CDCl3) δ ppm 0.55-0.61 (m, 2H), 0.90-0.97 (m, 2H), 1.69-1.77 (m, 1H), 7.00 (d, J=0.78 Hz, 1H), 7.49 (d, J=0.59 Hz, 1H), 9.58 (d, J=0.49 Hz, 1H).

Workup

  1. customPurification by flash chromatography (0-60% EtOAc in heptane)

Sources & evidence

ORD record
ord-9760f07871ad43d4835d4b246fa4a925
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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