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

HRID 1815115Notes

Reaction equation

[CH:1]1([C:6]([OH:23])([C:17]#[C:18][Si](C)(C)C)[CH2:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[O:11][C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].[Cs+]>CO>[CH:1]1([C:6]([OH:23])([C:17]#[CH:18])[CH2:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[O:11][C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 6-(2-cyclopentyl-2-hydroxy-4-trimethylsilanyl-but-3-ynyl)-2,2-dimethyl-[1,3]dioxom-4-one (−27.5 mmol, crude material from step 1 above), CsF (7.6 g, 50.0 mmol), and MeOH (75 mL) was stirred at room temperature overnight. HPLC at this time still showed starting material, so the reaction was heated at 40° C. for an additional 4 hours, at which time all starting material had been consumed. The reaction was concentrated and purified by flash chromatography through silica, eluted with 30% ethylacetate/hexanes, yielding 4.0 g of product (61% yield for two steps). 1H NMR (CDCl3): δ 1.63 (m, 4H), 1.72 (s, 3H), 1.74 (s, 3H), 2.16 (m, 1H), 2.49 (s, 1H), 2.53 (s, 1H), 2.58 (s, 1H), 5.43 (s, 1H), ESIMS (M+Na+): 287.1.

Workup

customhad been consumed
concentrationThe reaction was concentrated
custompurified by flash chromatography through silica
washeluted with 30% ethylacetate/hexanes

Sources & evidence

ORD record: ord-5a987b34395549d4b80e572bbdba8c59
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878727B2

Reaction notes

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