Sodium borohydride → (4-Iodo-2-methoxy-pyridin-3-yl)methanol

HRID 2086342Notes

Reaction equation

HRID 2086342 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]=[O:11].[BH4-].[Na+]>CCO>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 100383814-Iodo-2-methoxynicotinaldehyde

Product 1

HCID 11437022(4-Iodo-2-methoxy-pyridin-3-yl)methanolYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure in Example 1, the reaction was carried out with 1b (1.88 g, 7.1 mmol) and NaBH4 (0.135 g, 3.56 mmol) in EtOH (40 mL) to afford 2b as a pale yellow oil (1.83 g, 97%). The crude product was sufficiently pure for the subsequent reaction. IR (CH2Cl2, NaCl,cm−1) 3391, 2946, 1561, 1459, 1380, 1019, 805; 1H NMR (300 MHz, CDCl3) δ2.43 (t, J=7 Hz,1H), 3.99 (s, 3H), 4.82 (d, J=7 Hz, 2H), 7.35 (d, J=5.4 Hz, 1H), 7.7 (d, J=5.4 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ54.29, 64.90, 112.12, 126.50, 128.15, 146.59, 161.71; HRMS (EI) m/z calcd for C7H8NO2I (M+) 264.9600, found 264.9598; LRMS (EI) m/z 265 (M+, 53), 250(84), 138(30), 84(100), 78(30).

Sources & evidence

ORD record
ord-983404a3ee514c3ea698555681e97fbb
Source dataset
uspto-grants-2004_04
Patent number
US06723853B2

Reaction notes

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