Hexane → HCID 57699817, compound

Temperature

-10 °C

To a stirred suspension of triphenyl{3-[(phenylmethyl)oxy]propyl}phosphonium bromide (20.74 g, 42.2 mmol) in THF (60 ml) at −15° C. under a nitrogen atmosphere was added n-butyl lithium, 1.6M in hexane (26.4 ml, 42.2 mmol) dropwise over 30 mins. The orange/red solution was stirred at −10° C. for 30 mins. A solution of 2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde (6 g, 42.2 mmol) in THF (10 ml) was added dropwise at −10° C. over 25 mins. The reaction mixture was then stirred at −10° C. for 15 mins and then gradually allowed to warm up to room temperature while stirring under nitrogen atmosphere for 16 hours. Ether (10 ml) was added and the suspension was filtered on Celite. The Celite was washed with ether (2×40 mL). The filtrate was concentrated under vacuum. The residue was purified by chromatography on silica (2×100 g) using a cyclohexane:ethyl acetate 0->25% gradient over 40 mins on a Flashmaster II. The fractions were analysed by TLC (revealed with a permanganate dip). The desired fractions were combined and concentrated under vacuum to yield the title compound as a colourless oil (7.46 g).

1. stirringThe reaction mixture was then stirred at −10° C. for 15 mins
2. temperatureto warm up to room temperature
3. stirringwhile stirring under nitrogen atmosphere for 16 hours
4. filtrationthe suspension was filtered on Celite
5. washThe Celite was washed with ether (2×40 mL)
6. concentrationThe filtrate was concentrated under vacuum
7. customThe residue was purified by chromatography on silica (2×100 g)
8. waitethyl acetate 0->25% gradient over 40 mins on a Flashmaster II
9. concentrationconcentrated under vacuum

ORD record

ord-9d2284c8e5d94c5d88f4942356bf95b3

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977344B2