5-tert-butyl-2-furoic acid synthesis

7synthesis methods

Product Name:5-tert-butyl-2-furoic acid
CAS Number:56311-39-8
Molecular formula:C9H12O3
Molecular Weight:168.19

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Yield: 69%

Reaction Conditions:

with n-butyllithium in tetrahydrofuran;hexane

Steps:

K.1 Step 1
Step 1 To a solution of 2-tert-butylfuran (4.5 g, 36 mmol) in anh. THF (60 mL) at -78° C. under N₂ was added n-butyllithium (1.6M in hexane, 25 mL, 40 mmol, 1.1 equiv) dropwise. After 30 min, the cooling bath was replaced with an ice bath and the mixture was stirred at 0° C. for 1 h. Dry CO₂, generated from dry ice and dried over an anhydrous Na₂SO₄ tower, was bubbled into the reaction mixture over 20 min at -78° C. and then at 0° C. The reaction mixture was acidified to pH 1 with a 1M HCl solution, then extracted with EtOAc. The organic layer was washed with a concentrated NaCl solution, dried (NaSO₄) and concentrated under reduced pressure to give 5-tert-butylfuran-2-carboxylic acid as a pale yellow solid (4.2 g, 69%): ¹H NMR (CDCl₃) δ1.29 (s, 9H), 6.11 (d 1H, J=3.3 Hz), 7.19 (d, 1H, J=3.3 Hz), 11.0 (br s, 1H).

References:

Bayer Corporation US6344476, 2002, B1

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