(Methoxymethylene)triphenylphosphorane → HCID 131734415, compound

To a stirred solution of (methoxymethylene)triphenylphosphorane (6.74 g, 21.99 mmol) in tetrahydrofuran (30 mL) was added drop-wise a solution of potassium tert-butoxide (3.08 g, 27.5 mmol) in THF at −30° C. under argon, and the mixture was stirred for 30 min. Then a solution of (R)-3′,4′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-naphthalene]-3′-carbaldehyde (4.0 g, 18.33 mmol) in THF was added drop-wise and reaction was stirred for 1 h at −30° C. Reaction was monitored by TLC. Reaction mixture quenched with water at −30° C. and allowed to RT, diluted with water (25 mL) and extracted with ethyl acetate (2×50 mL), dried over Na2SO4, filtered and concentrated to give crude product (8 g). The crude compound was purified with silica gel flash column chromatography (Biotage) to give (R)-3′-(2-methoxyvinyl)-3′,4′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-naphthalene] (3.5 g, 14.21 mmol, 78% yield) as colourless liquid; m/z 246.6.

1. customdrop-wise and reaction
2. stirringwas stirred for 1 h at −30° C
3. customReaction
4. customReaction mixture
5. customquenched with water at −30° C.
6. customallowed to RT
7. additiondiluted with water (25 mL)
8. extractionextracted with ethyl acetate (2×50 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customto give crude product (8 g)
13. customThe crude compound was purified with silica gel flash column chromatography (Biotage)

ORD record

ord-674dc801d3394626bcb1aeabf21294f9

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227919B2