Benzyl Bromide → Cyclohexanone, 4-[(phenylmethoxy)methyl]-

温度

0 °C

1,4-dioxaspiro[4.5]decan-8-ylmethanol (1.33 g, 7.72 mmol) was dissolved in DMF (14 mL) and then cooled to 0° C. To the solution was added NaH (0.402 g, 10.04 mmol) in portions and the mixture agitated at 10° C. for 1 h and then benzyl bromide (1.194 mL, 10.04 mmol) was added and the mixture agitated over 72 h. The reaction mixture was quenched with water and extracted with ether and the combined organic extracts dried (MgSO4), filtered and concentrated in vacuo and the crude product 8-((benzyloxy)methyl)-1,4-dioxaspiro[4.5]decane dissolved in acetonitrile (35 mL) and water (25 mL) and treated with 3N HCl (13 mL) and agitated at room temperature for 20 min upon which LCMS indicated desired product. The reaction mixture was quenched with 40 mmol aqueous NaOH and then extracted with EtOAc (200 mL) and the organic layer was washed with water and dried (MgSO4), filtered and concentrated in vacuo and the residue purified by flash chromatography (0-50% EtOAc/heptane) to afford 1.23 g of the desired product as a colorless syrup (73%). LCMS (m/z): 329.2 (MH+), 1.33 min.

1. stirringthe mixture agitated over 72 h
2. customThe reaction mixture was quenched with water
3. extractionextracted with ether
4. dry with materialthe combined organic extracts dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. dissolutionthe crude product 8-((benzyloxy)methyl)-1,4-dioxaspiro[4.5]decane dissolved in acetonitrile (35 mL)
8. additionwater (25 mL) and treated with 3N HCl (13 mL)
9. stirringagitated at room temperature for 20 min upon which LCMS
10. extractionextracted with EtOAc (200 mL)
11. washthe organic layer was washed with water
12. dry with materialdried (MgSO4)
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customthe residue purified by flash chromatography (0-50% EtOAc/heptane)

ORDレコード

ord-e8968c09beeb4e35af9faaa79f0bc8be

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09242996B2