Methanol → 5-Bromo-2,2-dimethylpentan-1-ol

HRID 969039Notes

Reaction equation

HRID 969039 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:12])([CH3:11])[C:6](OCC)=[O:7].[Li+].[BH4-].CO>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:12])([CH3:11])[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 10681333Ethyl 5-bromo-2,2-dimethylpentanoate

Product 1

HCID 111831775-Bromo-2,2-dimethylpentan-1-olYield 108.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the procedure given for the synthesis of 206e, 205a (94.0 g, 0.37 mol) was reduced with LiBH4 (12.97 g, 0.60 mol) and methanol (19.04 g, 0.60 mol) in CH2Cl2 (400 mL) to give 206a (78.0 g, 100%) as an oil. 1H NMR (DMSO-d6): δ 4.42 (s, 1H), 3.45 (t, 2H, J=6.6), 3.08 (s, 2H), 1.84-1.69 (m, 2H), 1.27 (t, 2H, J=8.3), 0.78 (s, 6H). 13C NMR (DMSO-d6): δ 69.7, 36.9, 35.7, 34.5, 27.4, 24.0.

Sources & evidence

ORD record
ord-1906027c75cf4657ae1f9acea5d96994
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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