Diethyl Ether → HCID 15204724, compound

HRID 1769057Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].C([Li])CCC.C[C:16]1[N:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+].C[CH2:27][O:28]CC>CCCCCC>[OH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([O:28][CH3:27])[C:2]=1[CH:22]([C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][N:21]=1)[OH:23]

Participants

Conditions

Temperature: -20 °C

Procedure

To a mixture of 28.3 g (0.15 mol) of o-bromobenzyl alcohol in 1 L of ether cooled to -20° C. was added in portions 32.5 ml (0.32 mol) of n-butyllithium (10M) in hexane over a 20 min period and the reaction mixture was stirred for 1 hr. The above reaction mixture was cooled to -20° C., 19.9 g (0.165 mol) of 6-methyl-2-pyridinecarboxaldehyde was added to the mixture, and the resulting reaction mixture was allowed to warm to room temperature. After 1 hour, ammonium chloride solution was added to the mixture. The diol was extracted with ethyl acetate, washed with brine, the ethyl acetate phase was dried over sodium sulfate, and the solvent was removed in vacuo to afford 21.9 g (70.5%) of 2-[1-hydroxy-(2'-hydroxymethyl)-benzyl]-6-methyl-pyridine (Formula XIII: R1 =6--CH3 ; R2 =R7 =H).

Workup

customThe above reaction mixture
temperaturewas cooled to -20° C.
customthe resulting reaction mixture
temperatureto warm to room temperature
waitAfter 1 hour
extractionThe diol was extracted with ethyl acetate
washwashed with brine
dry with materialthe ethyl acetate phase was dried over sodium sulfate
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-23bc03d54f264164ae98dd1c57ca3d6a
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380729

Reaction notes

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