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

HRID 873295Notes

Reaction equation

HRID 873295 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-041316d6d3044b57b96cc57d8b5b1fc7
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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