Isoquinoline-4-carbaldehyde → (Isoquinolin-4-yl)methanol

HRID 279240Notes

Reaction equation

HRID 279240 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[O:12])=[CH:3][N:2]=1.B.CSC>C1COCC1>[OH:12][CH2:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=[N:2][CH:3]=1

Participants

4

Reactant 2

HCID 10868870Isoquinoline-4-carbaldehydeHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 12746377(Isoquinolin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Isoquinolinecarboxaldehyde (1 mmole) (prepared by the method of: J. B. Wommack, T. G. Barbee, Jr., D. J. Thoennes, M. A. McDonald and D. E. Pearson, J. Heterocyclic Chem., 1969, 6, 243-245.) is dissolved in anhydrous THF (50 mL) and treated with borane-methyl sulfide (0.3 mmoles) (as described in: E. Mincione, J. Org. Chem., 1978, 43, 1829-1830) at 0° C. for 0.5-1 h and worked up in the usual way to give the title compound.

Sources & evidence

ORD record
ord-577be0b0b84a42acb9d78e31bd6f4cc8
Source dataset
uspto-grants-2002_03
Patent number
US06362188B1

Reaction notes

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