Tetrahydrofuran → HCID 11309708, compound

HRID 1006181Notes

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): δ 5.95-5.92 (m, 1H), 5.79 (dddd, J=17.1, 10.2, 6.6, 6.6 Hz, 1H), 5.06-4.92 (m, 2H), 2.66-2.54 (m, 2H), 2.48-2.37 (m, 4H), 2.15-2.04 (m, 2H), 1.69-1.54 (m, 2H), 1.53-1.39 (m, 2H). 13C NMR (75 MHz, CDCl3): δ 209.9, 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-4fc1b3d7cf0d45d39ae0fc879c6d6ce3
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787655B2

Reaction notes

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