Hydrochloric Acid → Methyl 2-(2-hydroxyphenyl)butanoate

HRID 1034293Notes

Reaction equation

HRID 1034293 reaction equation
[CH:1](NC(C)C)(C)[CH3:2].[Li]CCCC.C[Si](C)(C)[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24].C(I)C.Cl>C1COCC1.CCCCCC>[OH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]([CH2:1][CH3:2])[C:23]([O:25][CH3:26])=[O:24]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 7912DiisopropylamineHCID 24754724Methyl (2-trimethylsilyloxyphenyl)acetateHCID 178418339Butyllithium

Product 1

HCID 19023711Methyl 2-(2-hydroxyphenyl)butanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diisopropylamine (0.46 mL) in THF (3 mL) at 0° C. was added 1.6M BuLi in hexane (2.01 mL). After stirring for 30 minutes at 0° C., 2.74 mL of this solution was added to a solution of methyl (2-trimethylsilyloxyphenyl)acetate from Step 1, (357 mg) in THF (5 mL) at 0° C. After 20 minutes, ethyl iodide (0.144 mL) was added and the mixture was stirred for 18 hours at r.t. Then, 2 mL of 1N HCl was added and the resulting mixture was stirred for 30 minutes, extracted with EtOAc, washed twice with brine, dried over MgSO4, filtered, and evaporated to dryness, giving the title compound.

Workup

  1. waitAfter 20 minutes
  2. stirringthe mixture was stirred for 18 hours at r.t
  3. stirringthe resulting mixture was stirred for 30 minutes
  4. extractionextracted with EtOAc
  5. washwashed twice with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-7b8203c7ce654298bd406dd5e817d57a
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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