Tetrahydrofuran → HCID 11309708, compound

HRID 991962Notes

Reaction equation

C1COCC1.Br[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].C[O:14][C:15]1[CH2:19][CH2:18][C:17](=O)[CH:16]=1>C(OCC)(=O)C>[CH2:7]([C:17]1[CH2:18][CH2:19][C:15](=[O:14])[CH:16]=1)[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

Conditions

Temperature: 60 °C

Procedure

Mg turnings (972 mg, 40 mmol) were placed into a dry Schlenk flask, then THF (20 mL) was added. 6-Bromo-1-hexene (5.3 mL, 40 mmol) was placed into a separate dry flask, dissolved in THF (20 mL), then added via syringe to the Mg solution. The resulting mixture was heated at 60° C. for 12 h, then cooled to room temperature. The solution of the Grignard reagent was then separated from remaining Mg solid by transferring the solution via syringe to another Schlenk flask. The general procedure for the preparation of substrates using 3-methoxycyclopentenone (2.24 g, 20 mmol) and the solution of the Grignard reagent described above gave, after 24 h and and flash chromatography (4:1 hexanes:ethyl acetate), the title compound as a colorless liquid (2.67 g, 81%). 1H NMR (300 MHz, CDCl3): δ5.95-5.92 (m, 1 H), 5.79 (dddd, J=17.1, 10.2, 6.6, 6.6 Hz, 1 H), 5.06-4.92 (m, 2 H), 2.66 -2.54 (m, 2 H), 2.48-2.37 (m, 4 H), 2.15 -2.04 (m, 2 H), 1.69-1.54 (m, 2 H), 1.53-1.39 (m, 2 H). 13C NMR (75 MHz, CDCl3): δ6209.9, 182.9, 138.3, 129.4, 114.8, 35.4, 33.5, 33.4, 31.6, 28.6, 26.6. IR (neat): 2929, 2860, 1706, 1615, 1437, 1183, 994, 909, 839 cm−1.

Workup

customdry flask
dissolutiondissolved in THF (20 mL)
additionadded via syringe to the Mg solution
temperaturecooled to room temperature
customThe solution of the Grignard reagent was then separated
customThe general procedure for the preparation of substrates
customabove gave, after 24 h

Sources & evidence

ORD record: ord-c8114fe7c7dd4b18a3f5fb7dfb3301aa
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465664B1

Reaction notes

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