Sodium hydride → trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[2-oxofuran-4(5H)-yloxy]-2H-1-benzopyran-6-carbonitrile

HRID 1460616Notes

Reaction equation

HRID 1460616 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].[OH:8][C@H:9]1[C@H:14](OC2CCC(=O)C=2)[C:13]2[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=[CH:25][C:12]=2[O:11][C:10]1([CH3:29])[CH3:28].[H-].[Na+]>O1CCCC1>[OH:8][C@H:9]1[C@H:14]([O:3][C:2]2[CH2:4][O:5][C:6](=[O:7])[CH:1]=2)[C:13]2[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=[CH:25][C:12]=2[O:11][C:10]1([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 129348Sdz pco 400HCID 521261Tetronic acid

Product 1

HCID 14301308trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[2-oxofuran-4(5H)-yloxy]-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

601 mg of tetronic acid and 1.01 g of the epoxide of example 1 are reacted analogously to example 6 with 180 mg of sodium hydride (80%) and 747 mg of borontrifluoride-diethyletherate in tetrahydrofurane. Usual work up yields white crystalls of the title compound. m.p. 111°-114° C. (dichloromethane/ether)

Sources & evidence

ORD record
ord-c790d8eee90d47818a0780194ea3da25
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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