Pivaloyl chloride → 1-Benzothiophen-6-YL 2,2-dimethylpropanoate

HRID 732816

Reaction equation

HRID 732816 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:2]1=2.[CH3:11][C:12]([CH3:17])([CH3:16])[C:13](Cl)=[O:14]>N1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][C:8]([O:10][C:13](=[O:14])[C:12]([CH3:17])([CH3:16])[CH3:11])=[CH:9][C:2]1=2

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 88004Benzo(b)thiophene-6-ol

Product 1

HCID 690681281-Benzothiophen-6-YL 2,2-dimethylpropanoateYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve benzo[b]thiophen-6-ol (10 g, 67 mmol) in pyridine (300 mL). Add 2,2-dimethyl-propionyl chloride (38 mL, 308 mmol) dropwise, and stir at room temperature for 8 hours. Concentrate in vacuo to ¼ volume, partition between ethyl acetate (250 mL) and water (250 mL). Separate layers, wash organic layer with water (250 mL) and brine (200 mL). Dry with magnesium sulfate, filter, and concentrate in vacuo to give 15 g of 2,2-dimethyl-propionic acid benzo[b]thiophen-6-yl ester (98%).

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition between ethyl acetate (250 mL) and water (250 mL)
  3. washSeparate layers, wash organic layer with water (250 mL) and brine (200 mL)
  4. dry with materialDry with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b9162a7dbdd346cf923519bd1c60a8fd
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Linked notes

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