Hydrochloric Acid → 6-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one

HRID 858651

Reaction equation

C([O:8][C:9]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)([CH2:12][C:13]1[O:18][C:17]([CH3:20])([CH3:19])[O:16][C:15](=[O:21])[CH:14]=1)[C:10]#[CH:11])(=O)C(OCC)=O.C([O-])([O-])=O.[K+].[K+].Cl>CO>[CH:22]1([C:9]([OH:8])([C:10]#[CH:11])[CH2:12][C:13]2[O:18][C:17]([CH3:20])([CH3:19])[O:16][C:15](=[O:21])[CH:14]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 23 °C

Procedure

To the optically pure (+)-1-cyclopentyl-1-[(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)methyl]prop-2-ynyl ethyl oxalate (2.5 g, 15.1 mmol) in 50 ml of MeOH was added K2CO3 (2.0 g). The mixture was stirred at 23° C. for 8 h. After complete conversion, the mixture was neutralized with 1N HCl at cold temperature. The aqueous solution was extracted with MTBE (×3) and the organic layer was washed with brine and dry over MgSO4. After removal of MTBE, 1.75 g of the desired product (+ enantiomer) was produced with 95.5% ee and 96% yield.

Workup

extractionThe aqueous solution was extracted with MTBE (×3)
washthe organic layer was washed with brine
dry with materialdry over MgSO4
customAfter removal of MTBE, 1.75 g of the desired product (+ enantiomer)
customwas produced with 95.5% ee and 96% yield

Sources & evidence

ORD record: ord-3041fb96acf446e6876b4d34838b18c3
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Linked notes

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