Sodium Sulfate → HCID 13020118, compound

HRID 867086Notes

Reaction equation

HRID 867086 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:22])([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][C:11](OCC)=[O:12])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)([OH:22])[CH2:10][CH2:11][OH:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 13020117HCID 13020117, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13020118HCID 13020118, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The base (9.5 g, 0.027 moles) from ethyl 3-(4-bromophenyl)-3-hydroxy-3-(3-pyridyl)propanoate hydrochloride (step 1) was prepared and dissolved in ethyl ether (50 ml). This solution was added dropwise to an ice-cold mixture of lithium aluminium hydride (1.0 g, 0.027 moles) and ethyl ether (150 ml). The reaction mixture was refluxed for 5 hours, cooled and a saturated sodium sulphate solution was added until a white precipitate was formed. This was filtered off and the filtrate evaporated. The residue was crystallized from chloroform. 1-(4-bromophenyl)-1-(3-pyridyl)-1,3-propanediol was obtained. Yield: 39%. M.p. 130°-132° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. temperaturecooled
  3. customwas formed
  4. filtrationThis was filtered off
  5. customthe filtrate evaporated
  6. customThe residue was crystallized from chloroform

Sources & evidence

ORD record
ord-4347759158c4491bb65ffd5264337d83
Source dataset
uspto-grants-1978_07
Patent number
US04102887

Reaction notes

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