Nitrogen → HCID 22905873, compound

HRID 2257252Notes

Reaction equation

HRID 2257252 reaction equation
Br[C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[O:13][CH2:14][CH2:15]Br.N#N.C([Li])CCC.CCCCCC.[NH4+].[Cl-]>O1CCCC1.CCCCCC.CO.CCOCC>[C:9]([C:4]1[C:3]2[O:13][CH2:14][CH2:15][C:2]=2[CH:7]=[CH:6][CH:5]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

8

Reactant 5

HCID 947NitrogenHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 22905874HCID 22905874, compoundHCID 178418339Butyllithium

Product 1

HCID 22905873HCID 22905873, compound

Reagents, catalysts & solvents 2

HCID 21864698Diethyl ether methanolSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

A cold solution of 1,5-dibromo-2-(2-bromoethoxy)-3-tert-butylbenzene (5.00 g, 12.05 mmol) in tetrahydrofuran/hexane (100 mL/20 mL) is cooled to -95° C. (MeOH/Et2O, liquid N2). A solution of n-butyl lithium in hexane (12 mL, 30.1 mmol) is added dropwise, and the reaction is allowed to stir for 0.5 h between -95° C. and -80° C. After 4 h, the reaction is poured onto saturated NH4Cl, and extracted with ethylacetate. The organic layer is washed twice with H2O and once with brine. The combined organic layers are dried (MgSO4), filtered, and evaporated. The resulting oil is purified by chromatography over SiO2 using hexanes. The resulting oil is distilled at reduced pressure to give 7-tert-butyl-2,3-dihydrobenzo[b]furan as a low melting white solid.

Workup

  1. waitAfter 4 h
  2. extractionextracted with ethylacetate
  3. washThe organic layer is washed twice with H2O and once with brine
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting oil is purified by chromatography over SiO2
  8. distillationThe resulting oil is distilled at reduced pressure

Sources & evidence

ORD record
ord-a9f000b2544742d28babbda48987e172
Source dataset
uspto-grants-1997_08
Patent number
US05656661

Reaction notes

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