Lithium Hydroxide → HCID 71499468, compound

HRID 633667Notes

Reaction equation

[OH:1][C@@H:2]1[C@@:9]([CH3:16])([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C@@H:8]2[C:17](=[O:18])[C@@:4]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])([C:5]([O:20]C)=[CH:6][C:7]2=[O:19])[CH2:3]1.[OH-].[Li+]>>[OH:20][C:5]1[C@:4]2([CH2:22][CH:23]=[C:24]([CH3:25])[CH3:26])[C:17](=[O:18])[C@@H:8]([C@:9]([CH3:16])([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C@@H:2]([OH:1])[CH2:3]2)[C:7](=[O:19])[CH:6]=1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 86718445HCID 86718445, compound

Product 1

HCID 71499468HCID 71499468, compoundYield 98%

Procedure

Prepared according to representative procedure on a scale of 0.037 mmol of 20 (13.2 mg) and 0.421 mmol of lithium hydroxide (10.1 mg). The crude material was filtered through silica gel using 10:1 dichloromethane:methanol as the eluent to give 53 as a white solid in a 98% yield (12.4 mg). 1H NMR (500 MHz, CDCl3) δ ppm 5.68 (s, 1H), 5.07 (t, J=7.0 Hz, 1H), 4.99 (t, J=6.3 Hz, 1H), 3.78 (dd, J=5.3, 11.8 Hz, 1H), 3.19 (s, 1H), 2.44 (ddd, J=7.3, 14.7, 39.0 Hz, 2H), 2.29-2.16 (m, 1H), 2.05-1.92 (m, 2H), 1.81 (t, J=12.5 Hz, 1H), 1.67 (s, 3H), 1.64 (s, 3H), 1.63 (s, 3H), 1.62 (s, 3H), 1.40-1.29 (m, 2H), 0.95 (s, 3H). HRMS-ESI (m/z): [M+Na]+ calculated for C21H30O4, 369.2036. found 369.2034.

Workup

customPrepared
filtrationThe crude material was filtered through silica gel using 10:1 dichloromethane

Sources & evidence

ORD record: ord-ac4b11cc1121436190b39a67d7103a3f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321713B2

Reaction notes

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