Ethyl Bromide → HCID 86668670, compound

Temperature

-38 °C

890 mg (127 mmol) of granulated lithium were added within 5 minutes to 100 ml (4.0 mol) of liquid ammonia at −40° C. The mixture was stirred until no more lithium floated (after approximately 10 minutes). A dark blue solution of lithium in liquid ammonia was obtained. 5.94 g (86.6 mmol) of isoprene was added portion wise within 10 minutes, whereas the solution gets white at the end of the addition. The mixture was stirred for 25 minutes at −38° C. 9.1 g (69.5 mmol) of 2-methoxy-2-prop-2-ynyloxy-butane (97.4% GC) were added with a dropping funnel to the reaction mixture at −38° C. within 25 minutes. The reaction mixture was held at −38° C. for about 1 hour. 14 g (128.5 mmol) of bromoethane were added with a dropping funnel to the reaction mixture within 20 minutes. The reaction mixture was subsequently stirred for 1 hour. 100 ml of n-hexane were added to the reaction mixture and the liquid ammonia was evaporated under normal pressure within 1 hour and 30 minutes. 50 ml of water was added to the reaction mixture at 40° C., and the mixture was stirred until all salt was dissolved. The mixture is transferred into a separatory funnel and the layers were separated. The aqueous layer is extracted with 127 ml of n-hexane. The organic layers were dried over 0.5 g of anhydrous sodium sulphate and concentrated under reduced pressure (40° C., 60 mbar), and the crude product (1-(1-methoxy-1-methyl-propoxy)-pent-2-yne) was analyzed by GC. 10.54 g of crude 1-(1-methoxy-1-methyl-propoxy)-pent-2-yne were obtained with a purity of 87.1% (yield 77.6% based on 2-methoxy-2-prop-2-ynyloxy-butane).

1. additionwhereas the solution gets white at the end of the addition
2. waitThe reaction mixture was held at −38° C. for about 1 hour
3. stirringThe reaction mixture was subsequently stirred for 1 hour
4. customthe liquid ammonia was evaporated under normal pressure within 1 hour and 30 minutes
5. addition50 ml of water was added to the reaction mixture at 40° C.
6. stirringthe mixture was stirred until all salt
7. dissolutionwas dissolved
8. customThe mixture is transferred into a separatory funnel
9. customthe layers were separated
10. extractionThe aqueous layer is extracted with 127 ml of n-hexane
11. dry with materialThe organic layers were dried over 0.5 g of anhydrous sodium sulphate
12. concentrationconcentrated under reduced pressure (40° C., 60 mbar)

ORD record

ord-97a97e3248484287b6d7ca73851c8f61

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045404B2