Water → (6-Iodo-5-methoxypyridin-2-yl)methanol

HRID 55276Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[N:20]=[C:19]([I:21])[C:18]([O:22][CH3:23])=[CH:17][CH:16]=1)=O.C(O)(C)C.O>C1(C)C=CC=CC=1.O1CCCC1>[OH:12][CH2:13][C:15]1[N:20]=[C:19]([I:21])[C:18]([O:22][CH3:23])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -70 °C

Procedure

40 ml of a 25% solution of diisobutylaluminum hydride in toluene is added drop by drop to a solution of 7 g of 2-iodo-3-methoxypyridine-6-carboxylic acid methyl ester in 95 ml of toluene and 50 ml of tetrahydrofuran at -70° C. The reaction mixture is stirred for 30 minutes at -70° C., heated to -5° C. within two hours and stirred for 2 hours at this temperature. The reaction mixture is cooled to -70° C., mixed in succession with 20 ml of isopropanol and 20 ml of water and stirred for three hours at room temperature. The precipitate is suctioned off on diatomaceous earth, the filter residue is washed with dichloromethane and the filtrate is concentrated by evaporation. 6.54 g of 6-hydroxymethyl-2-iodo-3-methoxypyridine of melting point 106°-108° C. is obtained.

Workup

temperatureheated to -5° C. within two hours
stirringstirred for 2 hours at this temperature
temperatureThe reaction mixture is cooled to -70° C.
stirringstirred for three hours at room temperature
washthe filter residue is washed with dichloromethane
concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record: ord-30ed483f116d457da5fce53a19b52087
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624943

Reaction notes

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