Hydrochloric Acid → HCID 67896168, compound

HRID 1196669Notes

Reaction equation

HRID 1196669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][CH:15]([C:17]([OH:19])=[O:18])[CH2:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH:20]([N-]C(C)C)(C)[CH3:21].[Li+].C([Li])CCC.C(NC(C)C)(C)C.C(I)C.Cl>O1CCCC1.CCCCCC.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[C@H:16]([CH2:20][CH3:21])[C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 19898995HCID 19898995, compoundHCID 178418339Butyllithium

Product 1

HCID 67896168HCID 67896168, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

A solution of 1.73 g (0.00625 mol) of 3-(4-chlorophenyl)-4,5,6,7-tetrahydro-1,2-benzisoxazole-6-carboxylic acid in 30 ml of dry tetrahydrofuran was added slowly at -70° C. to a solution of lithium diisopropylamide prepared by adding 5.25 ml of a 2.5M solution of n-butyllithium in hexane to 1.32 g (0.013 mol) of diisopropylamine in 20 ml of dry tetrahydrofuran at -70° C. After 0.25 hour a deep red color had developed. 1.05 g (0.0067 mol) of ethyl iodide in 5 ml of dry tetrahydrofuran were added and the temperature was allowed to rise to -20° C. over a period of 1.25 hours. The resulting light brown solution was poured into an excess of water and acidified with 2N hydrochloric acid. The mixture was extracted four times with diethyl ether and the combined ether extracts were washed with sodium chloride solution, dried over magnesium sulfate and evaporated. The residue was crystallized twice from glacial acetic acid and there was obtained 0.36 g of trans-3-(4-chlorophenyl)-7-ethyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-6-carboxylic acid of melting point 162°-163° C.

Workup

  1. customprepared
  2. waitto rise to -20° C. over a period of 1.25 hours
  3. extractionThe mixture was extracted four times with diethyl ether
  4. washthe combined ether extracts were washed with sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was crystallized twice from glacial acetic acid

Sources & evidence

ORD record
ord-bab4f788056d4cc7930a555f094e3ada
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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