Hydrochloric Acid → HCID 131720364, compound

HRID 398307Notes

Reaction equation

HRID 398307 reaction equation
[H-].[Na+].[C:3]([C:8]1[CH:22]=[CH:21][C:11]([CH2:12]P(=O)(OCC)OCC)=[CH:10][CH:9]=1)([O:5][CH2:6][CH3:7])=[O:4].[CH:23]([C:25]1[C:34]([O:35][CH2:36][CH2:37][CH3:38])=[CH:33][C:32]2[C:31]([CH3:40])([CH3:39])[CH2:30][CH2:29][C:28]([CH3:42])([CH3:41])[C:27]=2[CH:26]=1)=O.Cl>O1CCCC1.CS(C)=O>[CH3:39][C:31]1([CH3:40])[CH2:30][CH2:29][C:28]([CH3:41])([CH3:42])[C:27]2[CH:26]=[C:25](/[CH:23]=[CH:12]/[C:11]3[CH:10]=[CH:9][C:8]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:22][CH:21]=3)[C:34]([O:35][CH2:36][CH2:37][CH3:38])=[CH:33][C:32]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10979490Ethyl 4-((diethoxyphosphoryl)methyl)benzoateHCID 23002518HCID 23002518, compound

Product 1

HCID 131720364HCID 131720364, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

1.3 g of sodium hydride, 50% in mineral oil, were suspended in 20 ml of abs. dimethyl sulphoxide (DMSO) and treated dropwise at 15° C. with a solution of 8.6 g of diethyl (4-carbethoxybenzyl)-phosphonate in 25 ml of abs. DMSO. The mixture was stirred at room temperature for 1 hour and then a solution of 3.3 g of the above aldehyde in 25 ml of abs. DMSO and 10 ml of tetrahydrofuran was added dropwise thereto. After stirring at 40° C. for 2 hours the mixture was poured into ice-water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. After drying the organic phase with sodium sulphate and evaporation of the solvent the crude product was filtered over a silica gel column (eluent hexane/5% methyl tert.butyl ether). After recrystallization from hexane/ethyl acetate there were obtained 4.4 g of ethyl (E)-4-[2-(5,5,8,8-tetra-methyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate in the form of white crystals, melting point 97-100° C.

Workup

  1. stirringAfter stirring at 40° C. for 2 hours the mixture
  2. extractionextracted with ethyl acetate
  3. customAfter drying the organic phase
  4. customwith sodium sulphate and evaporation of the solvent the crude product
  5. filtrationwas filtered over a silica gel column (eluent hexane/5% methyl tert.butyl ether)
  6. customAfter recrystallization from hexane/ethyl acetate there

Sources & evidence

ORD record
ord-67646fbceca745f884338ca917cf1e65
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Reaction notes

Loading…