Hydrochloric Acid → HCID 67939631, compound

HRID 1196668Notes

Reaction equation

HRID 1196668 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)([CH3:22])[CH3:21].[Li+].C([Li])CCC.C(NC(C)C)(C)C.C(I)(C)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]([CH:20]([CH3:22])[CH3:21])[C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 19898995HCID 19898995, compoundHCID 178418339Butyllithium

Product 1

HCID 67939631HCID 67939631, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 0.865 g (0.0031 mol) of 3-(4-chlorophenyl)-4,5,6,7-tetrahydro-1,2-benzisoxazole-6-carboxylic acid in 20 ml of dry tetrahydrofuran was added slowly at -70° C. to a solution of lithium diisopropylamide prepared by adding 2.65 ml of a 2.5M solution of n-butyllithium in hexane to 0.66 g (0.0065 mol) of diisopropylamine in 20 ml of dry tetrahydrofuran at -70° C. After 0.25 hour a deep red solution had formed. 0.53 g (0.0031 mol) of isopropyl iodide in 5 ml of dry tetrahydrofuran was added and the mixture was stirred at -65° C. to -30° C. for 1 hour and at a temperature up to 5° C. for an additional 1 hour. The resulting yellow 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 and dried over magnesium sulfate. Evaporation gave a yellow solid which, after crystallization from glacial acetic acid, yielded 0.53 g of trans-3-(4-chlorophenyl)-4,5,6,7-tetrahydro-7-isopropyl-1,2-benzisoxazole-6- -carboxylic acid of melting point 180°-182° C.

Workup

  1. customprepared
  2. customAfter 0.25 hour a deep red solution had formed
  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. customEvaporation
  7. customgave a yellow solid which
  8. customafter crystallization from glacial acetic acid

Sources & evidence

ORD record
ord-daae5740318847f18c1943ca81a167ae
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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