Tetrahydrofuran → (R)-6-bromohexan-2-ol

HRID 266691Notes

Reaction equation

HRID 266691 reaction equation
Cl[C@H]([B:8]([O-:10])[O-:9])CCC[CH2:6][Br:7].[CH3:11][Mg]Br.[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1>>[BH:8]([O-:10])[O-:9].[Br:7][CH2:6][CH2:16][CH2:15][CH2:14][C@H:18]([OH:17])[CH3:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 86749941(R)-1-chloro-5-bromopentylboronateHCID 178418573HCID 178418573, compound

Product 2

HCID 54186641(R)-6-bromohexan-2-olHCID 178514824HCID 178514824, compound

Procedure

The Grignard reaction was performed, as in example 2, with the following amounts: DICHED (R)-1-chloro-5-bromopentylboronate, 20.04 g; 3.0N methylmagnesium bromide, 16.7 ml; 150 ml of THF. The oxidation of the DICHED boronate to give (R)-6-bromohexan-2-ol was performed by dissolving the DICHED 5-bromo-1-methylpentylboronate in THF (10 ml) in a 50 ml flask. Water (10 ml) was added and the solution. The solution was cooled to 0° C. while stirring under argon. Sodium carbonate (16.5 ml of a 3M solution) was added, followed by 8 ml of 30% hydrogen peroxide. The solution was filtered, 20 ml of pentane added, and filtered again. The aqueous phase was separated and washed with pentane (2×10 ml). The organic phase was dried over sodium sulfate, filtered and the solvent evaporated to give (R)-6-bromo-hexan-2-ol in a crude yield of 8.9 g. Vacuum distillation provided a yield of 7.1 g (84%) of pure material with a rotation of -13.89 [α]549.

Workup

  1. customThe Grignard reaction

Sources & evidence

ORD record
ord-4ed7588f8c914a5191bcc02de6c6987e
Source dataset
uspto-grants-1997_07
Patent number
US05652243

Reaction notes

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