Ethyl 7-bromo-2,2-dimethylheptanoate → 7-Bromo-2,2-dimethylheptan-1-ol

Temperature

0 °C

To a solution of ethyl 7-bromo-2,2-dimethylheptanoate (example 102, step a) (1.5 g) in dry diethyl ether (50 mL) at 0° C. under N2 was added diisobutylaluminium hydride (1M in toluene, 12.5 mL) dropwise. The reaction mixture was stirred at 0° C. for 1 h then quenched by addition of saturated potassium sodium tartrate (150 mL). The mixture was stirred for 1 h then extracted with ethyl acetate (×3). The combined organics were washed with brine and 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 1.16 g.

1. customthen quenched by addition of saturated potassium sodium tartrate (150 mL)
2. stirringThe mixture was stirred for 1 h
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-0a313f3291604dadb9d5f1b1faa92438

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2