Water → HCID 68281550, compound

HRID 1484532Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:13].[OH2:20].[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH2:1]([O:20][C:8]1[CH:7]=[C:6]([O:24][CH2:23][C:22]2[CH:21]=[CH:25][CH:11]=[CH:10][CH:9]=2)[CH:11]=[CH:10][C:9]=1[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[OH:13])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:4][CH:3]=1

Participants

Reactant 5

HCID 962Water

HCID 8028Tetrahydrofuran

HCID 8058Hexane

HCID 142732-Pyridinecarboxaldehyde

HCID 178418339Butyllithium

Product 1

HCID 68281550HCID 68281550, compound

Conditions

Temperature: -78 °C

Procedure

1.6 M n-butyllithium solution in hexane (9.3 ml; 14.9 mmol; 1.1 eq) is added dropwise to a solution of compound (12) (5 g; 13.5 mmol; 1.0 eq) in 130 ml of anhydrous THF cooled to −78° C. The solution is stirred for 1 hour at −78° C. and then 2-formylpyridine (4.5 ml; 47.3 mmol; 3.5 eq) is added dropwise. The solution is stirred for 3 hours at −78° C., then for 15 hours at room temperature, and then 800 ml of water is added. The precipitate obtained is filtered using a Buchner funnel, dried under vacuum and then purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 7:3) to lead to compound (13) (3.65 g; 70%) obtained as a beige solid.

Workup

stirringThe solution is stirred for 3 hours at −78° C.
waitfor 15 hours at room temperature
customThe precipitate obtained
filtrationis filtered
customdried under vacuum
custompurified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 7:3)
customobtained as a beige solid

Sources & evidence

ORD record: ord-5224ff476f6247669ad74f398ecaf9a8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422261B2

Reaction notes

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