Potassium tert-butoxide → 5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexan]-3-one

HRID 1965035Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (5-bromo-2-fluorophenyl)(1-hydroxy-4-methoxycyclohexyl)methanone (Intermediate 12 Step 2, 1.05 g, 3.17 mmol) and potassium tert-butoxide (0.445 g, 3.80 mmol) in THF (10 mL) was heated in a microwave reactor at 70° C. for 30 min. The solvent was removed in vacuo and the residue was purified by flash chromatography using a gradient of 0 to 15% EtOAc in hexanes to afford 388 mg (39% yield) of the title compound. 1H NMR (400 MHz, CDCl3): δ ppm 1.71 (m, 6 H), 2.31 (m, 2 H), 3.32 (m, 1 H), 3.41 (s, 3 H), 7.03 (d, J=9.20 Hz, 1 H), 7.36 (t, J=8.80, 2.00 Hz, 1 H), 7.77 (d, J=2.00 Hz, 1 H); MS (ES+) m/z 312 [M+H]+.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-ac482730ba0844099c727e0fba8a15ac
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415483B2

Reaction notes

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