Ethyl Acetate → (2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-7-chloro-6-(4-ethylbenzyl)-2,2-dimethyl-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]

HRID 1713614Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH2:52][C:53]2[CH:58]=[CH:57][C:56]([CH2:59][CH3:60])=[CH:55][CH:54]=2)=[CH:4][C:5]([C@@:9]2([CH2:48][C:49]([CH3:51])=[CH2:50])[C@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[O:10]2)=[C:6]([OH:8])[CH:7]=1.CCOC(C)=O>ClC(Cl)C.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[CH2:16]([O:15][C@@H:14]1[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:11]([CH2:39][O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:10][C@:9]21[C:5]1[C:6](=[CH:7][C:2]([Cl:1])=[C:3]([CH2:52][C:53]3[CH:58]=[CH:57][C:56]([CH2:59][CH3:60])=[CH:55][CH:54]=3)[CH:4]=1)[O:8][C:49]([CH3:51])([CH3:50])[CH2:48]2)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 25 (48 mg, 58 μmol) and silver triflate (15 mg, 58 μmol) in dichloroethane (1 mL) was heated to 70° C. for 2 h. LC/MS indicated that the conversion was complete to give a new and less polar component. After cooling, the mixture was loaded onto a TLC plate and developed using 10% EtOAc in petroleum ether to give 56 (19 mg, 40%). LC/MS m/z 846 (M+Na), 824 (M+1).

Workup

customto give a new and less polar component
temperatureAfter cooling

Sources & evidence

ORD record: ord-1708eec37d344a43afc3012e6311fc19
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795228B2

Reaction notes

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