Triethylamine → 3-{3-[2-(5-Phenyl-furan-2-yl)-vinyl]-phenyl}-acrylic acid

HRID 659110Notes

Reaction equation

HRID 659110 reaction equation
O[CH:2]([C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)[CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1.CS(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[C:20]1([C:17]2[O:16][C:15]([CH:2]=[CH:3][C:4]3[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=3)=[CH:19][CH:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 684146793-{3-[2-Hydroxy-2-(5-phenyl-furan-2-yl)-ethyl]-phenyl}-acrylic acid

Product 1

HCID 684119543-{3-[2-(5-Phenyl-furan-2-yl)-vinyl]-phenyl}-acrylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To acid (28) (9.2 mg, 0.028 mmol) in DCM (1 mL), externally cooled to −78° C., was added methanesulphonyl chloride, (20 mg, 0.17 mmol) and triethylamine (29 mg, 0.29 mmol). The solution was then allowed to warm to ambient temperature and stirred for a further 2 hours. The solvent was concentrated in vacuo and the residue purified by Flash Master Jones Chromatography using a 2 g silica cartridge and eluting with 50% EtOAc in heptane to give the title compound as a white solid. Yield: 3.6 mg, 41%; LC-MS tr 1.77 min; NMR Purity: >85%; MS (ES+) m/z 317 (M+H); 1H NMR (400 MHz; DMSO): δ 6.70-6.80 (m, 2H), 7.15 (d, 1H), 7.25-7.35 (d, 1H), 7.35-7.45 (m, 2H), 7.50-7.60 (m, 4H), 7.65-7.75 (m, 3H), 7.90 (d, 2H), 8.10 (s, 1H)

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue purified by Flash Master Jones Chromatography
  3. washeluting with 50% EtOAc in heptane

Sources & evidence

ORD record
ord-5a0486bb6a4b4a438647de3af78feccf
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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