Pyridine → HCID 21286948, compound

HRID 2231388Notes

Reaction equation

N1C=CC=CC=1.[C:7](Cl)(=[O:9])[CH3:8].CC[C@H:13](O)[C@@H:14]([C:16]1[O:22][C@@H:21]([CH3:23])[C@@H:20]([CH3:24])[C:18](=[O:19])[C:17]=1[CH3:25])[CH3:15].CN(C)C=[O:30]>>[CH3:23][CH:21]1[CH:20]([CH3:24])[C:18](=[O:19])[C:17]([CH3:25])=[C:16]([C:14]([CH3:13])([O:30][C:7](=[O:9])[CH3:8])[CH3:15])[O:22]1

Participants

Reactant 4

HCID 1049Pyridine

HCID 6228Dimethylformamide

HCID 6367Acetyl chloride

HCID 11020597HCID 11020597, compound

Product 1

HCID 21286948HCID 21286948, compoundYield 90%

Conditions

Temperature: 25 °C

Procedure

After adding 7.9 g (0.1 moles) of pyridine and 7.8 g (0.1 moles) of acetyl chloride to 100 ml of dehydrated dimethylformamide and cooling the mixture with ice, 11.3 g (0.05 moles) of stegobiol were dripped and agitated at 20° at 25° C. for 10 hours to provide 12.1 g of 2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-1-acetoxyethyl)-4H-pyran-4-on. The yield was 90%.

Sources & evidence

ORD record: ord-67ab82fc3ee94db2a5a566e6aa440fef
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04782168

Reaction notes

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