Ethyl Acetate → HCID 69198447, compound

HRID 1968407

Reaction equation

[CH3:1][C:2]([O:4][CH2:5][C@H:6]1[O:11][C@H:10](Br)[C@H:9]([O:13][C:14]([CH3:16])=[O:15])[C@@H:8]([O:17][C:18]([CH3:20])=[O:19])[C@@H:7]1[O:21][C:22]([CH3:24])=[O:23])=[O:3].[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29](/[CH:35]=[CH:36]/[C:37]2[CH:38]=[CH:39][C:40]([OH:43])=[CH:41][CH:42]=2)[CH:28]=1.C(OCC)(=O)C>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)(Cl)Cl.[OH-].[Na+]>[C:22]([O:21][CH:7]1[CH:8]([O:17][C:18](=[O:19])[CH3:20])[CH:9]([O:13][C:14](=[O:15])[CH3:16])[CH:10]([O:43][C:40]2[CH:39]=[CH:38][C:37](/[CH:36]=[CH:35]/[C:29]3[CH:30]=[C:31]([O:33][CH3:34])[CH:32]=[C:27]([O:26][CH3:25])[CH:28]=3)=[CH:42][CH:41]=2)[O:11][CH:6]1[CH2:5][O:4][C:2](=[O:3])[CH3:1])(=[O:23])[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of acetobromo-α-D-glucose (48 mg, 0.11 mM) and benzyltriethylammonium bromide (13 mg, 0.04 mM) in chloroform was added a solution of pterostilbene (30 mg, 0.11 mM)) in 1.25 M (2.5 mL) of NaOH. The mixture was stirred at 60° C. for 5 h and after a second addition of 10 mg of acetobromo-α-D-glucose and 1.0 mL of NaOH) the mixture was stirred at 60° C. for additional 5 h. Ethyl acetate was added and the organic phase was washed with water. The crude mixture was purified using flash chromatography eluting with ethyl acetate/hexanes (3:2) and afforded (E)-2-(acetoxy-methyl)-6-(4-(3,5-dimethoxystyryl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate.

Workup

stirringwas stirred at 60° C. for additional 5 h
washthe organic phase was washed with water
customThe crude mixture was purified
washeluting with ethyl acetate/hexanes (3:2)

Sources & evidence

ORD record: ord-1b30e9048f834828bdeaaab8034badb9
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426369B2

Linked notes

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