Pivaloyl chloride → 2,2-Dimethyl-propionic acid 2-[4-(2,2-dimethyl-propionyloxy)-phenyl]-benzofuran-5-yl ester

HRID 1794529Notes

Reaction equation

HRID 1794529 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl.N1C(=O)CC[C@H]1C(O)=O.C(Cl)Cl>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1)=[O:23]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 6569362-(4-Hydroxy-phenyl)benzofuran-5-OL

Product 1

HCID 235173722,2-Dimethyl-propionic acid 2-[4-(2,2-dimethyl-propionyloxy)-phenyl]-benzofuran-5-yl esterYield 64.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 131724524CH2Cl2 PyrSolvent

Procedure

A solution of 75 (8.2 g, 36.3 mmol) in CH2Cl2/Pyr was treated with pivaloyl chloride (9.63 g, 79.9 mmol) and stirred at rt until TLC indicated that the reaction was complete. The reaction was worked up by diluting with additional CH2Cl2 and washing with 2 N HCl aq. The CH2Cl2 layer was washed with satd NaHCO3 aq, brine and dried over MgSO4. Filtration and concentration yielded 9.3 g of the crude solid that was used as is for the next reaction.

Workup

  1. washwashing with 2 N HCl aq. The CH2Cl2 layer
  2. washwas washed with satd NaHCO3 aq, brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-ad7fee75a8b6490fb2e63f9520dbf91d
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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