Hydrochloric Acid → HCID 86750448, compound

HRID 975328Notes

Reaction equation

HRID 975328 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+].Br[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].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][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[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 84580Ethyl 5-bromovalerateHCID 19971743HCID 19971743, compound

Product 1

HCID 86750448HCID 86750448, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolvent2×HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

A solution containing 10.0 g (0.036 moles) of 6-acetoxy-3,4-dihydro-2-ethyl-2-hydroxy-5,7,8-trimethyl-2H-1-benzopyran in 100 ml of benzene and 30 ml of dimethylsulfoxide is rapidly dripped, under nitrogen atmosphere, into a suspension containing 1.0 g (0.040 moles) of 97% sodium hydride in 50 ml of dimethylsulfoxide. The solution, after 60 minutes, is cooled to 5° C. and added, by slow dripping, to 50 ml of benzene containing 8.3 g (0.040 moles) of ethyl 5-bromovalerate, while keeping a temperature lower than 25° C. After 24 hours the reaction mixture is diluted with ethyl ether and water, acidified with a 10% aqueous solution of hydrochloric acid and the crude product is recovered by evaporating the organic layer. The pure product, 9.06 g with a yield of 62%, obtained in form of a thick oil by chromatography on a column of silica gel with eluent methylene chloride-ethyl ether in 96:4 ratio, shows the following chemical-physical characteristics:

Workup

  1. additionadded
  2. customlower than 25° C
  3. customthe crude product is recovered
  4. customby evaporating the organic layer
  5. customThe pure product, 9.06 g with a yield of 62%, obtained in form of a thick oil by chromatography on a column of silica gel with eluent methylene chloride-ethyl ether in 96:4 ratio

Sources & evidence

ORD record
ord-909e041cc6aa4e6c99e6bf1de00452b8
Source dataset
uspto-grants-1997_03
Patent number
US05608084

Reaction notes

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