Sodium Hydroxide → 4-(3-Pyridyl)cyclohex-3-en-1-one ethylene acetal

HRID 1821161Notes

Reaction equation

S(Cl)(Cl)=O.[CH2:5]1[O:21][C:8]2([CH2:13][CH2:12][C:11](O)([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)[O:7][CH2:6]1.[OH-].[Na+]>N1C=CC=CC=1>[CH2:6]1[O:7][C:8]2([CH2:13][CH2:12][C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][CH2:9]2)[O:21][CH2:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

Thionyl chloride (45 mL, 622.5 mmol) was slowly added to a solution of 4-hydroxy-4-(3-pyridyl)cyclohexanone ethylene ketal (prepared as in step a, 29.3 g, 124.5 mmol) in pyridine (250 mL) at −10° C. After stirring at 0° C. for 2.5 h, the reaction mixture was poured onto ice and adjusted to pH 8 with 2 N NaOH. The aqueous layer was extracted with CH2Cl2 (100 mL×3) and the combined organic layers were washed with brine (200 mL), dried with MgSO4, and concentrated in vacuo to afford crude 4-(3-pyridyl)cyclohex-3-en-1-one ethylene ketal, which was used without further purification.

Workup

additionthe reaction mixture was poured onto ice
extractionThe aqueous layer was extracted with CH2Cl2 (100 mL×3)
washthe combined organic layers were washed with brine (200 mL)
dry with materialdried with MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e49fa3592f104f93be61e5109c81c53d
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605289B2

Reaction notes

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