Methanol → 5-Bromo-2-methyl-2-phenylpentan-1-ol

HRID 969040Notes

Reaction equation

HRID 969040 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6](OCC)=[O:7].[Li+].[BH4-].CO>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 23431358Ethyl 5-bromo-2-methyl-2-phenyl-pentanoate

Product 1

HCID 113458925-Bromo-2-methyl-2-phenylpentan-1-olYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the procedure given for the synthesis of 206e, 205b (23.70 g, 79.21 mmol) was reduced with LiBH4 (3.45 g, 158.4 mmol) and methanol (5.24 g, 163.5 mmol) in anhydrous CH2Cl2 (150 mL) to give 206b (20.0 g, 98%) as an oil. 1H NMR (CDCl3): δ 7.34-7.14 (m, 5H), 3.60 (m, 1H), 3.48 (m, 1H), 3.29 (t, 2H, J=6.0), 1.96-1.44 (m, 5H), 1.32 (s, 3H). 13C NMR (CDCl3): δ 144.25, 128.59, 126.71, 126.41, 72.44, 43.15, 37.06, 34.64, 27.58, 21.61. HRMS (LSIMS, nba): Calcd for C12H16Br (MH+-H2O): 239.0435, found: 239.0444.

Sources & evidence

ORD record
ord-f0ddec68e78141b0b556e812780a48bd
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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