2-(4-(Hydroxymethyl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione synthesis
- Product Name:2-(4-(Hydroxymethyl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
- CAS Number:1072960-82-7
- Molecular formula:C12H14BNO5
- Molecular Weight:263.0543
4408-64-4
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Yield:1072960-82-7 98%
Reaction Conditions:
in benzene; for 20 h;Dean-Stark;Reflux;
Steps:
4-(Hydroxymethyl)phenylboronic Acid MIDA Ester 4
An oven-dried flask topped with a Dean-Stark apparatus and condenserwas charged sequentially with 4-(hydroxymethyl)phenylboronicacid (3; 200 mg, 1.32 mmol), MIDA (387 mg, 2.63 mmol), anhydbenzene (2.7 mL), and DMSO (0.3 mL). The Dean-Stark trap was filledwith benzene and the resulting mixture was heated at reflux for 20 h(reaction monitored by TLC). The solution was cooled to rt, concentratedunder reduced pressure, and the resulting residue was purifiedby flash column chromatography (silica gel, EtOAc/acetone 8:2) toprovide compound 4 (340 mg, 98%); Rf = 0.35 (EtOAc/acetone 8:2)1H NMR (400 MHz, CD3CN): = 2.49 (s, 3 H), 3.91 (d, J = 17.2 Hz, 2 H),4.11 (d, J = 17.2 Hz, 2 H), 4.57 (s, 2 H), 7.34 (d, J = 8.0 Hz, 2 H), 7.45 (d,J = 8.0Hz, 2 H).13C NMR (100 MHz, CD3CN): = 41.4, 62.8, 64.6, 127.2, 133.5, 144.2,169.6.11B NMR (128 MHz, CD3CN): = 11.59.HRMS (ESI+): m/z [M + H]+ calcd for C12H14NO5B: 264.1043; found:264.1039.
References:
Debiais, Mégane;Müller, Sabine;Smietana, Michael;Vasseur, Jean-Jacques [Synthesis,2020,vol. 52,# 2,p. 2962 - 2969]
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