Ethyl Acetate → (2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-6-chloro-5-(4-ethylbenzyl)-3',4',5',6'-tetrahydro-2H-spiro[benzofuran-3,2'-pyran]-2-one

HRID 1713606Notes

Reaction equation

HRID 1713606 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:43]1[CH:44]=[C:45]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[C:46]([Cl:48])=[CH:47][C:42]=1[O:41][C@H:40]2[OH:58])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOC(C)=O>C(Cl)Cl>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:43]1[CH:44]=[C:45]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[C:46]([Cl:48])=[CH:47][C:42]=1[O:41][C:40]2=[O:58])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 68792761HCID 68792761, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 68792820(2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-6-chloro-5-(4-ethylbenzyl)-3',4',5',6'-tetrahydro-2H-spiro[benzofuran-3,2'-pyran]-2-oneYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 27 (8 mg, 10 μmol) in DCM was added pyridinium chlorochromate (9 mg, 42 μmol, 4.2 equiv). The mixture was stirred for 5 days until the reaction was complete. The mixture was directly loaded onto a preparatory TLC plate and developed using 15% EtOAc in petroleum ether to give 48 (5 mg, 62% yield). 1H NMR (300 MHz, CDCl3) δ 7.00-7.40 (m, 25H), 6.76 (d, J=6.6 Hz, 2H), 4.80-4.92 (m, 3H), 4.64 (d, J=10.8 Hz, 1H), 4.38-4.57 (m, 5H), 3.92-4.03 (m, 3H), 3.71-3.82 (m, 3H), 3.60 (dd, J=1.8, 11.1 Hz, 1H), 2.57 (q, J=7.5 Hz, 2H), 1.18 (t, J=7.5 Hz, 3H).

Sources & evidence

ORD record
ord-0f5104b4b0b244259b2bf5f041efda1f
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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