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

HRID 603508Notes

Reaction equation

HRID 603508 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH2:15][C:16]([O-])=[O:17])[C:12]([CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Li+].[BH4-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH2:15][CH2:16][OH:17])[C:12]([CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86644242[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-e4ecf8ff21fb4704ba28a3c59c0142ae
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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