Triethylamine → (3aR,4R,5R,6aS)-Hexahydro-2-oxo-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-4-carboxaldehyde

HRID 1598799Notes

Reaction equation

HRID 1598799 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@H:10]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:18])[O:7]2.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>ClCCl.CS(C)=O>[CH:2]([C@H:3]1[C@H:10]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:18])[O:7]2)=[O:1]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22842863HCID 22842863, compound

Product 1

HCID 11107879(3aR,4R,5R,6aS)-Hexahydro-2-oxo-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-4-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of Corey lactone, (1S,5R,6R,7R)-6-(hydroxymethyl)-7-(tetrahydropyranyioxy)-2-oxabicyclo[3.3.0]octan-3-one (1), (6.800 g) in dichloromethane (40 ml) was oxidized by means of Swern oxidetion with using a solution of oxalyl chloride (2M dichloromethan solution, 30 ml) in dichloromethane (100 ml), DMSO (8.45 ml), and triethylamine (16.9 ml). After the usual work up, Corey aldehyde, (1S,5R,6R,7R)-6-formyl-7-(tetrahydropyranyloxy)-2-oxabicyclo [3.3.0]octan-3-one (2) was obtained.

Sources & evidence

ORD record
ord-b1067328a6ac451e89f1dfb2a581d593
Source dataset
uspto-grants-1998_04
Patent number
US05739161

Reaction notes

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