Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acrylate → Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate

HRID 1798309Notes

Reaction equation

[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([C:13](=[CH2:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1>C(OCC)(=O)C.[C].[Pd]>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acrylate (1 g, 3.44 mmol, 1.00 equiv, 90%) and Palladium carbon (10%, 300 mg) in ethyl acetate (50 mL) was stirred for 1 h at 35° C. under a hydrogen atmosphere. The solid was filtered out and washed with 2×10 mL of THF. The filtrate was concentrated under vacuum. This resulted in 0.8 g (71%) of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate as a light-brown oil.

Workup

filtrationThe solid was filtered out
washwashed with 2×10 mL of THF
concentrationThe filtrate was concentrated under vacuum
customThis resulted in 0.8 g (71%) of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate as a light-brown oil

Sources & evidence

ORD record: ord-0c93e81b44d64fe8aecc68ab20a99b8f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

Loading…