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

HRID 239079Notes

Reaction equation

HRID 239079 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, 1 H), 3.45 (t, 2 H, J=6.6), 3.08 (s, 2 H), 1.84-1.69 (m, 2 H), 1.27 (t, 2 H, J=8.3), 0.78 (s, 6 H). 13C NMR (DMSO-d6); δ 69.7, 35.7, 34.5, 27.4, 24.0.

Sources & evidence

ORD record
ord-6814878b4f43447fa0d072233efb900e
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

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