Methanol → 7-Bromo-2,2-dimethylheptan-1-ol

HRID 969043Notes

Reaction equation

HRID 969043 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH3:14])([CH3:13])[C:8](OCC)=[O:9].[Li+].[BH4-].CO>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 11265571Ethyl 7-bromo-2,2-dimethylheptanoate

Product 1

HCID 113106207-Bromo-2,2-dimethylheptan-1-olYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the method for the synthesis of 206e, 205g (43.0 g, 0.16 mol) was treated with LiBH4 (5.55 g, 0.25 mol) and methanol (7.75 g, 0.24 mol) in CH2Cl2 (200 mL) to give 206g (36.2 g, 98%) as a colorless, viscous oil. 1H NMR (CDCl3): δ 3.41 (t, 2H, J=6.9), 3.30 (br. s, 2H), 1.90-1.84 (m, 3H), 1.42-1.22 (m, 6H), 0.86 (s, 6H). 13C NMR (CDCl3): δ 71.9, 38.6, 35.1, 34.1, 32.9, 29.2, 24.0, 23.2. HRMS (LSIMS, nba): Calcd for C9H18Br (MH+-H2O): 205.0592, found: 205.0563.

Sources & evidence

ORD record
ord-0874f2f8b2ab4b048f0304fc7d3fcb9e
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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