Nonanoic acid, 9-bromo-2,2-dimethyl-, ethyl ester → 9-Bromo-2,2-dimethylnonan-1-ol

Temperature

0 °C

To a solution of ethyl 9-bromo-2,2-dimethylnonanoate (example 103, step a) (1.27 g) in dry diethyl ether (40 mL) at 0° C. under N2 was added diisobutylaluminium hydride (1M in toluene, 9.5 mL) dropwise. The reaction mixture was stirred at 0° C. for 1.25 h then quenched by addition of saturated potassium sodium tartrate solution (150 mL). The mixture was stirred for 15 min then extracted with ethyl acetate (×3) then the combined organics were washed with brine, dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 0-25% ethyl acetate in cyclohexane to give the subtitled compound as a colourless liquid. Yield 0.56 g.

1. customthen quenched by addition of saturated potassium sodium tartrate solution (150 mL)
2. stirringThe mixture was stirred for 15 min
3. extractionthen extracted with ethyl acetate (×3)
4. washthe combined organics were washed with brine
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. customevaporated in vacuo
8. customPurification
9. washeluting with 0-25% ethyl acetate in cyclohexane

ORD record

ord-cdfcc47a857146b992f9428f6e56fde3

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2