Lithium Hydroxide → 2-(1,6-Dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

HRID 1798035Notes

Reaction equation

C([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[OH-].[Li+]>C1COCC1.O>[OH:11][B:9]1[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]=2[CH:6]([CH2:5][C:4]([OH:18])=[O:3])[O:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.835 g, 3.34 mmol) in THF (10 mL) was treated with lithium hydroxide (0.383 g, 16.70 mmol) in water (10 mL) at 0° C. The solution was stirred at 0° C. for 1 hour then quenched with 2N HCl to pH 2. The mixture was concentrated to approximately half of the entire volume. The solid that precipitated was collected by vacuum filtration, then rinsed with cold water and dried to give (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid as a light yellow solid (0.65 g, 88%). mp 165-166° C. 1H NMR (400 MHz, DMSO-d6) δ 12.31 (s, 1H), 9.30 (s, 1H), 9.08 (s, 1H), 6.88 (s, 1H), 6.66 (s, 1H), 5.38 (d, J=9.38 Hz, 1H), 3.00 (d, J=15.24 Hz, 1H), 2.20 (s, 3H), 2.00 (dd, J=15.24, 10.16 Hz, 1H). MS (ESI) m/z: 221 [M−1].

Workup

customthen quenched with 2N HCl to pH 2
concentrationThe mixture was concentrated to approximately half of the entire volume
customThe solid that precipitated
filtrationwas collected by vacuum filtration
washrinsed with cold water
customdried

Sources & evidence

ORD record: ord-e8c6047d5c094a4e837291bd14700e91
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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