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

HRID 873299Notes

Reaction equation

HRID 873299 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 C9H28Br (MH+−H2O): 205.0592, found: 205.0563.

Sources & evidence

ORD record
ord-380ae575b12f4b729386d48c7e7cbde3
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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