HCID 6435881, compound → HCID 67946281, compound

HRID 893552Notes

Reaction equation

HRID 893552 reaction equation
CC([CH:4]1[CH2:5][C:6]([C:8]2([CH:11]3O[CH:12]3[CH2:14][C:15]([CH:17]=[CH:18]1)=[CH2:16])[O:10]C2)=[O:7])C.CC1CCC=CC(=O)CCCC=1>CCOCC>[OH:10][CH:8]1[C:6](=[O:7])[CH:5]=[CH:4][CH2:18][CH2:17][C:15]([CH3:16])=[CH:14][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6435881HCID 6435881, compoundHCID 53995982HCID 53995982, compound

Product 1

HCID 67946281HCID 67946281, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Periplanone-B analogue of (4E, 8R, 9R, 10R)-8,9-epoxy-5-methyl-10,10-methylene-oxy-4-cyclodecen-1-one, suitable as cockroach attractant can be prepared by reacting 6-methyl-2,6-cyclodecadien-1-one with a silylating reagent under the presence of a basic catalyst to form a silyldienol ether, reacting the resultant ether with an organic peracid to obtain (2Z, 6E)-10-hydroxy-6-methyl-2,6-cyclodecadien-1-one, reacting the resultant product with a peroxide under the presence of a basic catalyst after protecting hydroxy groups thereof with protection groups to obtain an epoxide, reacting the epoxide with chloromethyl lithium or dimethyl sulfonium methylide thereby introducing a spiroepoxy group and then removing the protection groups, to obtain (1S, 4E, 8R, 9R, 10S)-8,9-epoxy-5-methyl-10,10-methyleneoxy-4-cyclodecen-1-ol and, further, oxidizing the resultant product with a chromic acid type or dimethyl sulfoxide type oxidizing agents.

Sources & evidence

ORD record
ord-d0bf4ed1f6ce4a08b89126a74ee19fe1
Source dataset
uspto-grants-1992_06
Patent number
US05126128

Reaction notes

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