Hexane → 4-(Benzo[d]oxazol-2-yl)phenol

HRID 2209644Notes

Reaction equation

HRID 2209644 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][Si](C(C)(C)C)(C)C)=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.Cl[C:28]1[O:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1>C1COCC1>[O:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=[C:28]1[C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 119862-ChlorobenzoxazoleHCID 4227167(4-Bromophenoxy)(tert-butyl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 27855874-(Benzo[d]oxazol-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-t-butyldimethylsilyloxybenzene (8.3 g; 29 mmol) in THF (60 ml) at -78° C. is added a solution of butyllithium in hexane (14 ml; 35 mmol) over 10 minutes. This is allowed to stir 1 hour and 2-chlorobenzoxazole (4 ml; 35 mmol) is added dropwise over 5 minutes.-After stirring 15 minutes, the reaction is allowed to warm to 0° C. and is quenched with MeOH. This is then poured into 1N HCl and after stirring 1 hour is extracted with ethyl acetate. The organic extracts are dried (MgSO4) and then concentrated to yield 4-(benzoxazol-2-yl)phenol which is used directly in Step C.

Workup

  1. stirring-After stirring 15 minutes
  2. customis quenched with MeOH
  3. additionThis is then poured into 1N HCl
  4. stirringafter stirring 1 hour
  5. extractionis extracted with ethyl acetate
  6. dry with materialThe organic extracts are dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-223830d509f04459b7f506d1caf3c42d
Source dataset
uspto-grants-1995_10
Patent number
US05455260

Reaction notes

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