2,5,5-Trimethyl-4-[(trimethylsilyl)oxy]cyclopent-2-en-1-one → HCID 54234765, compound

HRID 1395576Notes

Reaction equation

HRID 1395576 reaction equation
[CH3:1][C:2]1[C:3](=[O:14])[C:4]([CH3:13])([CH3:12])[CH:5]([O:7][Si:8]([CH3:11])([CH3:10])[CH3:9])[CH:6]=1>O1CCCC1>[CH3:1][C:2]1[C:3]([C:4]#[C:3][C:2]([CH3:1])=[CH:6][CH2:5][O:7][Si:8]([CH3:11])([CH3:9])[CH3:10])([OH:14])[C:4]([CH3:13])([CH3:12])[CH:5]([O:7][Si:8]([CH3:11])([CH3:10])[CH3:9])[CH:6]=1

Participants

3

Reactant 1

HCID 203400762,5,5-Trimethyl-4-[(trimethylsilyl)oxy]cyclopent-2-en-1-one

Product 1

HCID 54234765HCID 54234765, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The resulting 2,5,5-trimethyl-4-[(trimethylsilyl)oxyl]-cyclopent-2-en-1-one of formula VI is then condensed in a solvent (e.g. tetrahydrofuran) by means of a Grignard reaction with trimethyl-[(trans-3-methyl-pent-2-en-4-yn-1-yl)oxy]-silane of formula VII to give 5-[2,5,5-trimethyl-1-hydroxy-4-[(trimethylsilyl)oxy]-cyclopent-2-en-1-yl]-3-methyl-1-[(trimethylsilyl)oxy]-pent-2-en-4-yne of formula VIII which, without isolation, is saponified by shaking with a dilute aqueous alkali hydroxide solution to give 5-[1,4-dihydroxy-2,5,5-trimethyl-cyclopent-2-en-1-yl]-trans-3-methyl-pent-2-en-4-yn-1-ol of formula IX.

Sources & evidence

ORD record
ord-807b76f26f63487ca5b13425b7071ec5
Source dataset
uspto-grants-1980_05
Patent number
US04204073

Reaction notes

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