Water → HCID 86642021, compound

Sodium hydride (60% dispersion in mineral oil, 2.9 g, 72 mmol) and dimethylformamide (100 mL) were charged to a 250 mL three-necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added a solution of (2S)-6-methylheptan-2-ol (3.1 g, 24 mmol) in dimethylformamide (10 mL). This reaction mixture was stirred at room temperature for 1 hr then allyl bromide (8.6 g, 72 mmol) was added dropwise over 10 minutes ensuring the reaction temperature did not rise significantly (41° C. was observed). The reaction mixture was stirred for a further 20 minutes until the reaction was complete. To the reaction mixture was added water (10 mL) and the resultant mixture was extracted with methyltert-butyl ether (2×100 mL). The combined organic phase was dried over magnesium sulphate and the solvent remove in vacuo to yield a yellow oil which was chromatographed over silica gel (hexane/methyltert-butyl ether) to give 3-{[(1S)-1,5-dimethylhexyl]oxy}prop-1-ene as a sl. yellow oil (2.7 g, 15.8 mmol, chemical yield 66%).

1. customfitted with thermocouple, magnetic stirrer, condenser
2. customrise significantly (41° C. was observed)
3. stirringThe reaction mixture was stirred for a further 20 minutes until the reaction
4. extractionthe resultant mixture was extracted with methyltert-butyl ether (2×100 mL)
5. dry with materialThe combined organic phase was dried over magnesium sulphate
6. customthe solvent remove in vacuo
7. customto yield a yellow oil which
8. customwas chromatographed over silica gel (hexane/methyltert-butyl ether)

ORD record

ord-35f3c444aebf4d4dac5cb03c1e628c2a

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088725B2