Water → HCID 178447225, compound

HRID 1241694Notes

Reaction equation

HRID 1241694 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:9][CH:8]=1.C[O:21][B:22](OC)[O:23]C.O>C1COCC1>[BH:22]([OH:23])[OH:21].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8470Trimethyl borateHCID 182511Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-HCID 178418339Butyllithium

Product 1

HCID 178447225HCID 178447225, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(Method G-2) Under an atmosphere of nitrogen, n-butyllithium (22.75 mL, 2.2 eq) was slowly added to a solution of 4-chloropivaloylamino benzene (16.5 g, 0.078 mol) in dry THF (360 mL) at 0° C. After 2 hrs the mixture was cooled to −78° C. and trimethylborate (19.5 mL, 2.2 eq) slowly added. The mixture was allowed to warm to −15° C. and stirred for 2.5 hrs giving a clear colourless solution. Water (90 mL) was added, the lower, aqueous layer removed, washed with dichloromethane (150 mL) and acidified (90 mL 2M HCl) giving the title compound as a white solid (12.6 g, 0.049 mol, 63.2%). See, for example, Timari et al, 1996.

Workup

  1. temperatureto warm to −15° C.
  2. customgiving a clear colourless solution
  3. customthe lower, aqueous layer removed
  4. washwashed with dichloromethane (150 mL)

Sources & evidence

ORD record
ord-f154018727bf4c008e0502757c4c3bd1
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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