(2R)-1-Bromo-2,6-dimethylheptane → (2R,6R)-(+)-1-tert. Butoxy-2,6,10-trimethylundecane

HRID 26792Notes

Reaction equation

HRID 26792 reaction equation
Br[CH2:2][C@H:3]([CH3:10])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:9])[CH3:8].C1(C)C=CC(S(O[CH2:21][CH2:22][C@@H:23]([CH3:30])[CH2:24][O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=O)=O)=CC=1>>[C:26]([O:25][CH2:24][C@H:23]([CH3:30])[CH2:22][CH2:21][CH2:2][C@H:3]([CH3:10])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:9])[CH3:8])([CH3:27])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 13191839(2R)-1-Bromo-2,6-dimethylheptaneHCID 131710899(R)-(+)-4-tert. butoxy-3-methyl-1butanol p-toluenesulfonate

Product 1

HCID 12923314(2R,6R)-(+)-1-tert. Butoxy-2,6,10-trimethylundecane

Procedure

Reaction of the Grignard reagent, i.e., the magnesium salt of (R)-1-bromo-2,6-dimethylheptane with the (R)-(+ )-4-tert. butoxy-3-methyl-1-butanol p-toluenesulfonate was carried out using the procedure described in Example 12. The desired product (2R,6R)-(+)-1-tert. butoxy-2,6,10-trimethylundecane was obtained as a colorless oil, b.p. 90° C. (bath temperature) (0.1 mm Hg.).

Sources & evidence

ORD record
ord-8ab056e3531f4576b86827cb74abbac1
Source dataset
uspto-grants-1979_04
Patent number
US04151205

Reaction notes

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