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

HRID 646825Notes

Reaction equation

HRID 646825 reaction equation
BrCCCCC(C)(C1C=CC(C)=CC=1)CO.[Br:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[C:22](OCC)=[O:23].[Li+].[BH4-].CO>C(Cl)Cl>[Br:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[CH2:22][OH:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 10681333Ethyl 5-bromo-2,2-dimethylpentanoateHCID 111968926-Bromo-2-methyl-2-p-tolylhexan-1-ol

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-d): δ 69.7, 36.9, 35.7, 34.5, 27.4, 24.0.

Sources & evidence

ORD record
ord-a51285ed30e54fef92f81e66c2313246
Source dataset
uspto-grants-2010_04
Patent number
US07705177B2

Reaction notes

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