Sodium Hydroxide → HCID 57706234, compound

HRID 1662435Notes

Reaction equation

[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[C:11]([C:13](OC)=[O:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[F:25])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[O:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[F:25])[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution of 66.46F (452.7 mg, 1.3 mmol) in dry THF (10 mL) at 0° C. was added LAH (1.0 M in THF) (2.7 mL, 2.7 mmol) dropwise. Upon complete addition, the reaction was maintained at 0° C. and was monitored by TLC and LCMS. After 45 minutes, 1N NaOH was added to quench the reaction. The resulting solution was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was purified by flash chromatography (silica gel 60, eluted with 0%-50% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 66.46G as a colorless oil (330.4 mg, 80%). 1H NMR (400 MHz, CDCl3) δ ppm 7.33 (3H, m), 7.03 (1H, m), 6.84 (2H, m), 5.51 (1H, s), 4.69 (2H, s), 4.08 (2H, q, J=2.5 Hz), 3.77 (3H, s), 3.67 (2H, t, J=5.3 Hz), 3.00 (1H, s), 2.13 (2H, m).

Workup

additionUpon complete addition
customto quench
customthe reaction
extractionThe resulting solution was extracted three times with EtOAc
dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration
customthe residue was purified by flash chromatography (silica gel 60, eluted with 0%-50% EtOAc in hexanes)
additionFractions containing the desired product
concentrationconcentrated

Sources & evidence

ORD record: ord-a73527a713774f558772327bcf0c81d5
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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