HCID 67373569, compound → HCID 67374410, compound

HRID 1805926Notes

Reaction equation

[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]2[CH2:22][O:21]C(C3C=CC=CC=3)[O:19][CH2:18]2)=[CH:12][C:11]=1[O:29][CH:30]([CH3:32])[CH3:31])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CCOC(C)=O>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([CH2:18][OH:19])[CH2:22][OH:21])=[CH:12][C:11]=1[O:29][CH:30]([CH3:32])[CH3:31])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of 10% palladium on carbon (38.9 mg, 0.037 mmol) in a solution of 2-isopropoxy-4-[(2-phenyl-1,3-dioxan-5-yl)oxy]phenyl benzoate (158.7 mg, 0.365 mmol) in EtOAc (3.65 mL) was stirred under H2 (double balloon pressure) at 25° C. for 4 days. The reaction mixture was filtered through a plug of Celite and the filtrate was concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 100% EtOAc over 2394 mL) to afford 4-[2-hydroxy-1-(hydroxymethyl)ethoxy]-2-isopropoxyphenyl benzoate, as a colorless solid. Rf=0.17 (50% EtOAc in hexanes). LCMS calc.=347.15; found=347.06 (M+H)+. 1H NMR (500 MHz, CHCl3): δ 8.18 (d, J=7.8 Hz, 2 H); 7.61 (t, J=7.5 Hz, 1 H); 7.49 (t, J=7.7 Hz, 2 H); 7.03 (d, J=8.7 Hz, 1 H); 6.68 (d, J=2.7 Hz, 1 H); 6.56 (dd, J=8.8, 2.7 Hz, 1 H); 4.45 (p, J=6.1 Hz, 1 H); 4.34 (p, J=4.8 Hz, 1 H); 3.89-3.80 (m, 4 H); 2.88 (s, 2 H); 1.23 (d, J=6.1 Hz, 6 H).

Workup

filtrationThe reaction mixture was filtered through a plug of Celite
concentrationthe filtrate was concentrated in vacuo
customto afford the crude product
customThis was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 100% EtOAc over 2394 mL)

Sources & evidence

ORD record: ord-96d20d20758e45e984fb95181f3cf272
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354454B2

Reaction notes

Loading…