Sulfuric Acid → HCID 131723657, compound

HRID 1019238Notes

Reaction equation

HRID 1019238 reaction equation
[CH3:1][C:2]12[CH2:11][CH2:10][C@@H:9]([C:12]([CH3:14])=[CH2:13])[CH2:8][C:7]1=[CH:6][C:5](=[O:15])[CH2:4][CH2:3]2.S(=O)(=O)(O)[OH:17]>C(O)=O>[CH3:1][C:2]12[CH2:11][CH2:10][C@@H:9]([C:12]([OH:17])([CH3:14])[CH3:13])[CH2:8][C:7]1=[CH:6][C:5](=[O:15])[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12069822HCID 12069822, compound

Product 1

HCID 131723657HCID 131723657, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In Scheme V, treatment of (6R/S,9R)-6-methyl-9-(1-methylvinyl)-bicyclo[4,4,0]dec-1-ene-3-one (1) with mixture of sulfuric acid and formic acid at room temperature produces (6R/S,9R)-6methyl-9-(1-hydroxyisopropyl)-bicyclo[4.4.0]-dec-1-ene-3-one (14). Compound (14) reacts with organometallic reagent such Grignard reagent or organolithium reagent to form compound of formula (15) and the reaction is conducted in diethylether, tetrahydrofuran or any other solvent that does not interfere with the reaction at room temperature or cooled with ice bath or ice-salt mixture. Cyclization of compound of formula (15) to form compound of formula (Ie) is carried out in acidic medium, optionally with inorganic acid such as hydrochloric acid, sulfuric acid, or phosphoric acid in any solvent that does not interfere with the reaction such as water, methanol, ethanol, diethylether, benzene, toluene, methylene chloride, chloroform, ethylacetate, tetrahydrofuran, or a mixture thereof, particularly benzene-water, diethylether-water mixture. The reaction temperature is usually room temperature or lower.

Sources & evidence

ORD record
ord-7f1916d203254cefb9b965038008ea3c
Source dataset
uspto-grants-2002_11
Patent number
US06486201B1

Reaction notes

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