Lithium borohydride → 2-[6-(4-Methoxyphenyl)-3-methyl-2-pyridinyl]ethanol

HRID 2235974Notes

Reaction equation

HRID 2235974 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:7]=1)C.[Li+].[BH4-]>C1COCC1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[N:7]=[C:6]([CH2:5][CH2:4][OH:3])[C:11]([CH3:12])=[CH:10][CH:9]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 59300475Ethyl[6-(4-methoxyphenyl)-3-methyl-2-pyridinyl]acetate

Product 1

HCID 593004712-[6-(4-Methoxyphenyl)-3-methyl-2-pyridinyl]ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure described for the preparation of Example 470 and starting from [6-4-methoxyphenyl)-3-methyl-2-pyridinyl]acetate (Example 479, 0.25 g, 0.88 mmol), LiBH4(0.88 mL, 2 M in THF, 1.75 mmol) in THF (4.4 mL), the title compound was obtained (0.18 g, 84%). 1H NMR (400 MHz, CD2Cl2) δ 7.87 (d, 2H), 7.55-7.45 (m, 2H), 6.98 (d, 2H), 4.18-4.08 (m, 2H), 3.85 (s, 3H), 3.06-2.95 (m, 2H), 2.29 (s, 3H).

Workup

  1. customdescribed for the preparation of Example 470

Sources & evidence

ORD record
ord-bbe00d3959d648399b34c1c046d240c7
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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