Sodium;3-oxidodioxaborirane;tetrahydrate → 3-Cyano-4-{[(1R)-1-methylpropyl]oxy}benzoic acid

HRID 423325Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:11][C@H:12]([CH3:15])[CH2:13][CH3:14])=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:2].B1([O-])O[O:17]1.O.O.O.O.[Na+]>C(O)(=O)C>[C:8]([C:7]1[CH:10]=[C:3]([CH:4]=[CH:5][C:6]=1[O:11][C@H:12]([CH3:15])[CH2:13][CH3:14])[C:1]([OH:17])=[O:2])#[N:9]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-formyl-2-{[(1R)-1-methylpropyl]oxy}benzonitrile (D37) (310 mg, 1.53 mmol) in acetic acid (30 ml) was added sodium perborate tetrahydrate (471 mg, 3.05 mmol), the reaction mixture was heated at 50° C. over the weekend. The reaction mixture was concentrated in vacuo and water (˜50 ml) added, EtOAc (˜30 ml) was added and the layers partitioned, the aq layer was extracted twice more with EtOAc (˜30 ml) and the combined organics evaporated to dryness under reduced pressure to give the title compound (315 mg) as an off-white solid. δH (d6-DMSO, 400 MHz): 8.07-8.24 (2H, m), 7.38 (1H, d), 4.63-4.77 (1H, m), 1.55-1.83 (2H, m), 1.31 (3H, d), 0.95 (3H, t). MS (ES+): C12H13NO2 requires 219; found 220 (MH+).

Workup

concentrationThe reaction mixture was concentrated in vacuo and water (˜50 ml)
additionadded
additionEtOAc (˜30 ml) was added
customthe layers partitioned
extractionthe aq layer was extracted twice more with EtOAc (˜30 ml)
customthe combined organics evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-fe14328d6f82469f94c624f502b5b67e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101775B2

Reaction notes

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