Hydrochloric Acid → HCID 178514831, compound

HRID 1161174Notes

Reaction equation

HRID 1161174 reaction equation
C([Li])CCC.CCCCCC.Br[C:13]1[CH:14]=[C:15]([C:19]2[O:23][N:22]=[C:21]([OH:24])[CH:20]=2)[CH:16]=[CH:17][CH:18]=1.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C.Cl>C1(C)C=CC=CC=1.C1COCC1>[OH:24][C:21]1[CH:20]=[C:19]([C:15]2[CH:14]=[C:13]([B:25]([OH:30])[OH:26])[CH:18]=[CH:17][CH:16]=2)[O:23][N:22]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 178418339ButyllithiumHCID 178515525HCID 178515525, compound

Product 1

HCID 178514831HCID 178514831, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Add a 2.5 M solution of n-butyllithium in hexane (0.60 mL, 1.10 mmol) to a solution of 5-(3-bromophenyl)isoxazol-3-ol (120 mg, 0.50 mmol) and triisopropyl borate (113 mg, 0.60 mmol) in a mixture of toluene (2.5 mL) and THF (2.5 mL) at −78° C. After 1.5 h, warm the mixture to −20° C. and add a 2.0 N aqueous HCl solution (1 mL). Extract the mixture with EtOAc after warm to room temperature. Dry, filter and concentrate the organic layer to a white solid.

Workup

  1. extractionExtract the mixture with EtOAc
  2. temperatureafter warm to room temperature
  3. customDry
  4. filtrationfilter
  5. concentrationconcentrate the organic layer to a white solid

Sources & evidence

ORD record
ord-738494c5dfd14746894074d55de22c64
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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