Water → (2-Chloro-5-(pyridin-2-yl)phenyl)methanol

HRID 594220Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][C:9]=1[C:10](OC)=[O:11].O.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][C:9]=1[CH2:10][OH:11]

Participants

Conditions

Temperature: -10 °C

Procedure

A cooled (−10° C.) suspension of LiAlH4 (37 mg; 0.97 mmol) in anh. THF (1.5 ml) was treated with a solution of methyl 2-chloro-5-(pyridin-2-yl)benzoate (220 mg; 0.88 mmol) in anh. THF (1 ml). The mixture was further stirred at −10° C. for 20 min. Water (37 μl), 15% aq. NaOH (37 μl), and water (110 μl) were then successively added, and the resulting mixture was further stirred at rt for 1 h. Filtration, concentration to dryness under reduced pressure, and additional drying under HV afforded (2-chloro-5-(pyridin-2-yl)phenyl)methanol as a colorless solid. LC-MS (conditions A): tR=0.42 min.; [M+H]+: 219.94 g/mol.

Workup

temperatureA cooled
stirringthe resulting mixture was further stirred at rt for 1 h
filtrationFiltration, concentration to dryness under reduced pressure
customadditional drying under HV

Sources & evidence

ORD record: ord-534e17cba8e5474e9c80ab04ed2462be
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242970B2

Reaction notes

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