Pentaerythritol → HCID 71618850, compound

HRID 2276821Notes

Reaction equation

[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[OH-].[Na+].[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14]>CS(C)=O>[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][O:5][CH2:14][CH2:13][C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

To DMSO (100 mL) was added pentaerythritol 1 (68 g, 0.5 mol); the heterogeneous suspension was heated to 80° C. until the system became clear, then aqueous NaOH (4 g of NaOH in 9 mL of H2O) was added in one portion, tert-butyl acrylate (87 mL, 0.6 mol) was added to the solution dropwise, and vigorous stirring continued overnight at 80° C. After cooling, the solution was extracted with EtOAc. The combined organic phase was washed with H2O and brine, concentrated through rotary evaporation, and the residue was subjected to silica gel chromatography using CH2Cl2/MeOH as the eluent to give 2 (54.3 g, 0.21 mol, 41% yield) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 3.63 (br, 3H), 3.56 (t, J=5.5 Hz, 2H), 3.52 (s, 6H), 3.37 (s, 2H), 2.38 (t, J=5.0 Hz, 2H), 1.37 (s, 9H); 13C NMR (126 MHz, CDCl3) δ 171.7, 81.2, 72.1, 67.2, 63.6, 45.3, 36.1, 28.1; MS (ESI) m/z 209 (M−tBu+2H)+, 265 (M+H)+, 287 (M+Na)+; HRMS (ESI) calcd for C12H25O6 265.1651 (M+H)+, 209.1025 [M−tBu+2H]+. found 265.1646, 209.1026, respectively.

Workup

additionwas added to the solution dropwise
customvigorous stirring continued overnight
customat 80° C
temperatureAfter cooling
extractionthe solution was extracted with EtOAc
washThe combined organic phase was washed with H2O and brine
concentrationconcentrated through rotary evaporation

Sources & evidence

ORD record: ord-d9412f0733f548fd9a574ec32c9167d6
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133114B2

Reaction notes

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