Hydrochloric Acid → HCID 13553303, compound

HRID 622719Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2/[CH:16]=[CH:17]/[C@@H:18]2[O:23][C:22](=[O:24])[CH2:21][C@@H:20]([OH:25])[CH2:19]2)=[CH:4][C:3]=1[CH2:26][O:27][Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2/[CH:16]=[CH:17]/[C@@H:18]2[O:23][C:22](=[O:24])[CH2:21][C@@H:20]([OH:25])[CH2:19]2)=[CH:4][C:3]=1[CH2:26][OH:27]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of the compound (1i) (420 mg, 0.087 mmol) in THF (5 mL) was treated with tetrabutylammonium fluoride (1 M in THF, 2.5 mL, 2.5 mmol). After stirring at 20° C. for 5 minutes, 1 N HCl (100 mL) was added and the product was extracted into Et2O (125 mL). The organic layer was washed with H2O (2×100 mL), dried, filtered and evaporated to provide the desired compound as a faint yellow gum; homogeneous on TLC [Rf 0.20 vs 0.42 for the silyl ether (silica, CHCl3 -MeOH (19:1))] and HPLC [time of elution was 5.36 minutes with a flow rate of 4 mL/min using 20% isopropanol/hexane on a Whatman Partisil PXS 10/25 PAC column]. An analytical sample was crystallized from nBuCl: mp 137°-138° C.; NMR 1.7-1.95 (2 H, m), 2.33 (6 H, s), 2.45-2.75 (2 H, m), 4.05-4.1 (H, m), 4.7-4.85 (2 H, m), 5.12-5.18 (H, m), 5.4 (H, dd, J=7 and 15 Hz), 6.53 (H, d, J=15 Hz), 6.95-7.35 (6 H, m).

Workup

extractionthe product was extracted into Et2O (125 mL)
washThe organic layer was washed with H2O (2×100 mL)
customdried
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-32e3e02f68e04fbeb0cc5f46050cf981
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04772626

Reaction notes

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