Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 2-[3-(3-bromophenyl)cyclobutylidene]acetate

HRID 2240955Notes

Reaction equation

HRID 2240955 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][C:10](=O)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:13]([O:15][C:16](=[O:37])[CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:14]>ClCCl>[CH2:13]([O:15][C:16](=[O:37])[CH:17]=[C:10]1[CH2:11][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:9]1)[CH3:14]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 177501013-(3-Bromophenyl)cyclobutan-1-one

Product 1

HCID 59790338Ethyl 2-[3-(3-bromophenyl)cyclobutylidene]acetateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-Bromo-phenyl)-cyclobutanone (2.03 g 9.02 mmol) and Triphenyl-phosphoranylidene acetic acid ethyl ester (15.72 gms 45.12 mmol) were dissolved in dichloromethane (30 mL) inside a CEM 80 ml microwave vessel. The solution was irradiated in a CEM Discover™ microwave instrument for 30 minutes at 120° C. Pressure reached a maximum of 180 PSI. The product was purified by column chromatography (isocratic; 10% diethyl ether in hexanes) to give 2.37 gm of an oil (89%) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (t, J=7.1 Hz, 3H) 2.89-3.00 (m, 1H) 3.03-3.11 (m, 1H) 3.16-3.27 (m, 1H) 3.46-3.57 (m, 1H) 3.63 (q, J=8.0 Hz, 1H) 4.08 (q, J=7.0 Hz, 2H) 5.71 (q, J=2.9 Hz, 1H) 7.25-7.35 (m, 2H) 7.39-7.43 (m, 1H) 7.48-7.52 (m, 1H); MS (APPI) m/z 295 [M+H]·+.

Workup

  1. customThe solution was irradiated in a CEM Discover™ microwave instrument for 30 minutes at 120° C
  2. customThe product was purified by column chromatography (isocratic; 10% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-ca6bb444d6094d2799f801969c352dfe
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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