Diethyl Ether → HCID 18357478, compound

HRID 1422148Notes

Reaction equation

HRID 1422148 reaction equation
[O:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2Br)=[N:2]1.C([Li])CCC.C[CH2:23][O:24]CC>CCCCCC>[O:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:23]=[O:24])=[N:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 18357661HCID 18357661, compoundHCID 178418339Butyllithium

Product 1

HCID 18357478HCID 18357478, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 4.1 g of 2-(4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)-bromobenzene in 100 ml of ether at a temperature of -40° C. was added 11 ml of a 1.5M solution of butyllithium in hexane with magnetic stirring. The reaction was warmed to -20° C. and held at this temperature for 5 minutes. The lithio species was quenched by the addition of 1.3 ml of N,N-dimethylformamide. To the reaction was added 100 ml of saturated ammonium chloride and the solution was extracted with two 200 ml portions of ether. The combined organic layers were dried over sodium sulfate and evaporated to yield 3.5 g of 2-(4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)-benzaldehyde, GC-M.S. (E.I.) (M/Z): 226 [M-H]+.

Workup

  1. customThe lithio species was quenched by the addition of 1.3 ml of N,N-dimethylformamide
  2. additionTo the reaction was added 100 ml of saturated ammonium chloride
  3. extractionthe solution was extracted with two 200 ml portions of ether
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-136ddf1609af4775ae4a435e5bfec915
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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