Hydrochloric Acid → HCID 86750446, compound

HRID 975326Notes

Reaction equation

HRID 975326 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]2[O:13][C:12]([CH2:15][CH3:16])([OH:14])[CH2:11][CH2:10][C:9]=2[C:17]=1[CH3:18])(=[O:3])[CH3:2].[H-].[Na+].[CH:23]([O:26][C:27](=[O:35])[C:28]([CH3:34])([CH3:33])[CH2:29][CH2:30][CH2:31]Br)([CH3:25])[CH3:24].Cl>C1C=CC=CC=1.CS(C)=O.C(OCC)C.O>[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]([O:13][CH2:31][CH2:30][CH2:29][C:28]([CH3:33])([CH3:34])[C:27]([O:26][CH:23]([CH3:24])[CH3:25])=[O:35])=[C:9]([CH2:10][CH2:11][C:12](=[O:14])[CH2:15][CH3:16])[C:17]=1[CH3:18])(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 15688743HCID 15688743, compoundHCID 19971743HCID 19971743, compound

Product 1

HCID 86750446HCID 86750446, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolvent2×HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution containing 20.0 g (0.072 moles) of 6-acetoxy-3,4-dihydro-2-ethyl-2-hydroxy-5,7,8-trimethyl-2H-1-benzopyran in 500 ml of benzene is slowly dripped, under nitrogen atmosphere, into a suspension containing 2.07 g (0.086 moles) of 97% sodium hydride in 150 ml of dimethylsulfoxide. After 40 minutes the solution is dripped into a solution containing 21.6 g (0.086 moles) of 2,2-dimethyl-5-bromopentanoic acid isopropyl ester in 100 ml of benzene brought to 60° C. and the mixture is reacted for 3 hours at 60° C. Then the suspension is diluted with ethyl ether and water, acidified with a 10% aqueous solution of hydrochloric acid and the product is recovered by evaporation of the organic solvent and purified by chromatography on column of silica gel with eluent petroleum ether-ethyl ether in 60:40 ratio. After evaporation of the solvent, 16.6 g are obtained with a yield of 83% of an oil having the following chemical-physical characteristics:

Workup

  1. custombrought to 60° C.
  2. customthe mixture is reacted for 3 hours at 60° C
  3. customthe product is recovered by evaporation of the organic solvent
  4. custompurified by chromatography on column of silica gel with eluent petroleum ether-ethyl ether in 60:40 ratio
  5. customAfter evaporation of the solvent, 16.6 g

Sources & evidence

ORD record
ord-d9aa158fbc8f47548c117dadd9b93188
Source dataset
uspto-grants-1997_03
Patent number
US05608084

Reaction notes

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