Neopentyl glycol → 5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-thiophene-2-carboxylic acid

HRID 2110774Notes

Reaction equation

HRID 2110774 reaction equation
[OH:1][B:2]([OH:11])[C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.[CH3:12][C:13]([CH3:18])([CH2:16]O)[CH2:14]O>C1COCC1>[CH3:12][C:13]1([CH3:18])[CH2:16][O:1][B:2]([C:3]2[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=2)[O:11][CH2:14]1

Participants

4

Reactant 2

HCID 31344Neopentyl glycolHCID 27798075-Boronothiophene-2-carboxylic acid

Product 1

HCID 689325775-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-thiophene-2-carboxylic acidYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(Dihydroxyboryl)-2-thiophenecarboxylic acid (527 mg, 3.1 mmol) and 2,2-dimethyl-propane-1,3-diol (361 mg, 3.4 mmol) are stirred in THF (10 mL) for 19 hours and concentrated in vacuo to afford 5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-thiophene-2-carboxylic acid (748 mg) as a solid. LCMS: RT=1.15 minutes; 1H NMR [300 MHz, (CD3)2SO]: □13.15 (1H, s); 7.7 (1H, m); 7.45 (1H, m); 3.75 (4H, s); 0.95 (6H, s).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57d8912c5b804bc58627e78e6cdcc430
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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