Pivaloyl chloride → HCID 66934181, compound

HRID 1365622Notes

Reaction equation

HRID 1365622 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:19])=[C:16](Cl)[S:17][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>C1COCC1.CCCCCC>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:19])=[C:16]([C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])[S:17][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62493Pivaloyl chlorideHCID 58256121HCID 58256121, compoundHCID 178418339Butyllithium

Product 1

HCID 66934181HCID 66934181, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

The product from step (g) (109 mg, 0.35 mmol) in anhydrous THF (5 ml) was cooled to −78° C. under a nitrogen atmosphere and treated with 1.6 M n-butyl lithium in hexane (0.25 ml). The reaction mixture was stirred at −78° C. for 5 minutes followed by the addition of trimethyl acetyl chloride (0.22 ml, 1.75 mmol). After 10 additional minutes at −78° C., the reaction mixture was allowed to warm to room temperature. The reaction was quenched with saturated NaHCO3 (20 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), and solvent evaporated in vacuo to give the subtitled compound as an orange oil which was used in the next step without further purification. MS: ESI (positive): 362, 364 (M+H).

Workup

  1. customat −78° C.
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched with saturated NaHCO3 (20 ml)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. washThe combined organic extracts were washed with brine (50 ml)
  6. dry with materialdried (MgSO4), and solvent
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0c9f2725f11b4b258a37e273417088c9
Source dataset
uspto-grants-2011_02
Patent number
US07893051B2

Reaction notes

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