2-Bromobenzyl alcohol → 8-[2-(Hydroxymethyl)phenyl]-1,4-dioxaspiro[4.5]decan-8-ol

温度

-4 °C

To a solution of 2-bromobenzyl alcohol (3.0 g, 16 mmol) in THF (40 mL) cooled at −78° C. was added a 2.5 M solution of n-BuLi in hexanes (14.1 mL). The mixture was stirred at −4° C. for 1 hour and cooled back to −78° C. To it was added a solution of 1,4-cyclohexanedione mono-ethylene ketal (2.5 g, 16 mmol) in TIE (10 mL) over 15 minutes. Stirring was continued at −78° C. for 30 minutes and at −4° C. for 1 hour. The reaction was quenched by addition of a solution of NH4Cl in water. The resulting solution was extracted with EtOAc three times. The combined extract was washed with brine, dried over MgSO4 and concentrated. Purification on silica gel eluting with 5% MeOH/CH2Cl2 provided the title compound. MS calculated (M+H)+ 265, found 287 (M+Na)+.

1. temperaturecooled back to −78° C
2. stirringStirring
3. waitwas continued at −78° C. for 30 minutes and at −4° C. for 1 hour
4. customThe reaction was quenched by addition of a solution of NH4Cl in water
5. extractionThe resulting solution was extracted with EtOAc three times
6. extractionThe combined extract
7. washwas washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customPurification on silica gel eluting with 5% MeOH/CH2Cl2

ORDレコード

ord-a285c5cecc5441239cfa2db866ebbf76

出典データセット

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08729063B2