(R)-(+)-4-tert. butoxy-3-methyl-1butanol p-toluenesulfonate → (R)-(+)-1-tert. Butoxy-2,6-dimethylheptane

Reaction equation

C1(C)C=CC(S(O[CH2:11][CH2:12][C@@H:13]([CH3:20])[CH2:14][O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=O)=O)=CC=1.[CH2:22]([Mg]Br)[CH:23]([CH3:25])[CH3:24]>>[C:16]([O:15][CH2:14][C@H:13]([CH3:20])[CH2:12][CH2:11][CH2:22][CH:23]([CH3:25])[CH3:24])([CH3:17])([CH3:18])[CH3:19]

Participants

Reactant 2

HCID 131710899(R)-(+)-4-tert. butoxy-3-methyl-1butanol p-toluenesulfonate

HCID 178418816HCID 178418816, compound

Product 1

HCID 13206259(R)-(+)-1-tert. Butoxy-2,6-dimethylheptaneYield 76%

Procedure

Coupling of (R)-(+)-4-tert. butoxy-3-methyl-1butanol p-toluenesulfonate with isobutylmagnesium bromide was carried out using the procedure of Example 47. (R)-(+)-1-tert. Butoxy-2,6-dimethylheptane was obtained in 76% yield as a colorless liquid.

Sources & evidence

ORD record: ord-44f0d648d2414e618c16fa7d219a2cd8
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04051153

Reaction notes

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