ChemicalBook CAS DataBase List 3-Hydroxy-cyclobutanecarboxylic acid ethyl ester

3-Hydroxy-cyclobutanecarboxylic acid ethyl ester synthesis

5synthesis methods

Product Name:3-Hydroxy-cyclobutanecarboxylic acid ethyl ester
CAS Number:17205-02-6
Molecular formula:C7H12O3
Molecular Weight:144.17

87121-89-9
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3-Hydroxy-cyclobutanecarboxylic acid ethyl ester

17205-02-6
94 suppliers
$6.00/100mg

Yield: 93%

Reaction Conditions:

with methanol;sodium tetrahydroborate at 0; for 0.5 h;

Steps:

53.53B 53B. Ethyl 3 -hydroxy cyclobutanecarboxylate
53B. Ethyl 3 -hydroxy cyclobutanecarboxylate [00218] To a 0 °C solution of ethyl 3-oxocyclobutanecarboxylate (0.18 g, 1.27 mmol) in MeOH (10 mL) was added NaBH₄ (0.048 g, 1.27 mmol). The solution was stirred at 0 °C for 30 min and then quenched with 1 N aq. HC1. Volatiles were removed in vacuo, and the residue was partitioned between EtOAc and 1 N aq. HC1. The organic layer was dried (MgS0₄) and concentrated in vacuo to afford the title compound (0.17 g, 93% yield) as a mixture of the cis- and trans-isomers. ^lR NMR (500 MHz, CDCI3) δ 4.17 - 4.24 (m, 1H), 4.15 (d, J = 7.2 Hz, 2H), 2.54 - 2.66 (m, 3H), 2.1 1 - 2.22 (m, 2H), 1.27 (t, J = 7.2 Hz, 3H).

References:

BRISTOL-MYERS SQUIBB COMPANY;SHI, Yan;WANG, Ying;CHENG, Peter T.W.;WU, Shung C. WO2016/40223, 2016, A1 Location in patent:Paragraph 00218