Tetrahydrofuran → HCID 22676876, compound

HRID 991963Notes

Reaction equation

HRID 991963 reaction equation
[CH2:1]([C:7]1CCC(=O)[CH:8]=1)[CH2:2][CH2:3]CC=C.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1.C(C(Br)CCC[O:29][CH2:30][CH2:31][CH2:32][CH:33](Br)[CH2:34][C:35]1[CH:40]=CC=CC=1)C1C=CC=CC=1.C(OC1CCC(=O)C=1)C>C(OCC)(=O)C>[CH2:17]([O:16][CH:15]([CH3:14])[CH2:40][CH2:35][C:34]1[C:30](=[O:29])[CH2:31][CH2:32][CH:33]=1)[C:13]1[CH:8]=[CH:7][CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 897773-Ethoxycyclopent-2-en-1-oneHCID 11309708HCID 11309708, compoundHCID 53446386HCID 53446386, compound

Product 1

HCID 22676876HCID 22676876, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of a Grignard reagent was prepared following the procedure described in the synthesis of 3-(5-hexenyl)cyclopent-2-enone, using Mg turnings (302 mg, 12 mmol), THF (11 mL), and benzyl 4-bromobutylether (2.75 g, 11.3 mmol). The general procedure for the preparation of substrates using 3-ethoxycyclopentenone (0.67 mL, 5.65 mmol), gave, after 12 h and flash chromatography (3:1, then 2:1 hexanes:ethyl acetate), the title compound as a white solid (0.662 g, 48%). m.p. 46-47° C. 1H NMR (300 MHz, CDCl3): δ7.34-7.25 (m, 5 H), 5.94 (s, 1 H), 4.50 (s, 2 H), 3.49 (t, J=6.0 Hz, 2 H), 2.58-2.55 (m, 2 H), 2.41-2.38 (m, 3 H), 1.70-1.67 (m, 4 H). 13C NMR (75 MHz, CDCl3): δ210.2, 182.9, 138.6, 129.7, 128.6, 127.8 (2 peaks partially resolved), 73.3, 70.0, 35.6, 33.6, 31.8, 29.8, 24.2. IR (neat): 2941, 2853, 1710, 1613, 1451, 1366, 1185, 1119, 1000, 842, 749 cm−1.

Workup

  1. customThe general procedure for the preparation of substrates
  2. customgave, after 12 h

Sources & evidence

ORD record
ord-054f86b658b04220a2087f61381545c5
Source dataset
uspto-grants-2002_10
Patent number
US06465664B1

Reaction notes

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