Sodium hydride → HCID 63628074, compound

Temperature

68 °C

A solution of but-3-en-1-ol (96%, 28.0 mL, 312 mmol) in tetrahydrofuran (150 mL) was added to a suspension of sodium hydride (60% in mineral oil, 59.9 g, 1.50 mol) in tetrahydrofuran (700 mL) at 0° C. After the reaction mixture had stirred for 30 minutes at this temperature, a solution of 2-bromo-1,1-diethoxyethane (97%, 72.6 mL, 468 mmol) in tetrahydrofuran (150 mL) was added at 0° C., and the reaction mixture was heated to 68° C. for 66 hours. The reaction mixture was cooled to 0° C., slowly quenched with water (150 mL), and concentrated in vacuo to remove tetrahydrofuran. After three extractions with ethyl acetate, the combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the product as an oil, which was taken directly to the following step. Yield: 77 g. 1H NMR (400 MHz, CDCl3), product peaks only: δ 1.23 (t, J=7.0 Hz, 6H), 2.32-2.38 (m, 2H), 3.50 (d, J=5.3 Hz, 2H), 3.53-3.62 (m, 4H), 3.67-3.75 (m, 2H), 4.63 (t, J=5.3 Hz, 1H), 5.02-5.06 (m, 1H), 5.07-5.13 (m, 1H), 5.77-5.88 (m, 1H).

1. temperatureThe reaction mixture was cooled to 0° C.
2. customslowly quenched with water (150 mL)
3. concentrationconcentrated in vacuo
4. customto remove tetrahydrofuran
5. extractionAfter three extractions with ethyl acetate
6. dry with materialthe combined organic layers were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-044edf590a3f4297af1be6925b148fcb

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933221B2